Heterocyclic compound

ABSTRACT

A compound of formula (I), or an N-oxide thereof is provided. In the compound of formula (I), Het 1  represents Het 1 -1, Het 1 -2, Het 1 -3, Het 1 -4, Het 1 -5, Het 1 -6, Het 1 -7, Het 1 -8, or Het 1 -9, and the remaining variable groups are as defined in the specification. The compound of formula (I), or N-oxide thereof has a superior effect in controlling arthropod pests.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a Section 371 of International Application No.PCT/JP2017/012289, filed Mar. 27, 2017, which was published in theJapanese language on Oct. 12, 2017, under International Publication No.WO 2017/175613 A1, which claims priority under 35 U.S.C. § 119(b) toJapanese Application No. 2016-076517, filed Apr. 6, 2016, thedisclosures of which are incorporated herein by reference in theirentireties.

TECHNICAL FIELD

The present invention is related to a heterocyclic compound and an agentfor controlling harmful arthropod comprising the same.

BACKGROUND ART

To date, some compounds for controlling harmful arthropods have beendeveloped and come into practical use. Also, a certain class ofcompounds has been known to have an effect on controlling harmfularthropods (see, for example, Patent Document 1).

CITATION LIST Patent Document

-   Patent Document 1: Pesticide Science, 1987, 18, 179-190

SUMMARY OF THE INVENTION Problems to be Solved by Invention

An object of the present invention is to provide a compound having anexcellent efficacy for controlling harmful arthropods.

Means to Solve Problems

The present invention provides the following embodiments.

[1] A compound represented by formula (I):

wherein

Het¹ represents Het¹-1, Het¹-2, Het¹-3, Het¹-4, Het¹-5, Het¹-6, Het¹-7,Het¹-8, or Het¹-9:

R¹ represents OR⁴, OS(O)₂R⁴, S(O)_(m)R⁴, NR⁵S(O)₂R, a C1-C4 chainhydrocarbon group having one or more halogen atoms, or a halogen atom;

R⁴ represents a C1-C4 chain hydrocarbon group having one or more halogenatoms;

R⁵ represents a hydrogen atom, or a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms;

X¹ represents a nitrogen atom, or CR³⁰;

X² represents a nitrogen atom, or CR³¹;

X³ represents a nitrogen atom, or CR³²;

X⁴ represents a nitrogen atom, or CR³³;

X⁵ represents a nitrogen atom, or CR³⁴;

R³⁰, R³¹, R³², R³³, and R³⁴ represent independently of each other ahydrogen atom, a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a C3-C6 alicyclic group optionally having one ormore halogen atoms, or a halogen atom,

R^(1a) represents a C1-C6 chain hydrocarbon group optionally having oneor more halogen atoms, a C3-C6 alicyclic group optionally having one ormore halogen atoms, or a halogen atom;

r is 0, 1, 2, or 3, and when r is 2 or 3, two or more R^(1a) may beidentical to or different from each other;

A¹ represents a nitrogen atom, or CR⁹;

a combination of A², A³, and A⁴ represents a combination where A²represents CR⁶, A³ represents CR⁷, and A⁴ represents CR⁸,

a combination where A² represents a nitrogen atom, A³ represents CR⁷,and A⁴ represents CR⁸,

a combination where A² represents CR⁶, A³ represents a nitrogen atom,and A⁴ represents CR⁸, or

a combination where A² represents CR⁶, A³ represents CR⁷, and A⁴represents a nitrogen atom;

R⁹ represents a hydrogen atom, or a halogen atom;

R⁶, R⁷ and R⁸ represent independently of each other a hydrogen atom, aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a nitro group, OR¹⁸, NR¹⁸R¹⁹, a cyano group, or a halogen atom;

n is 0, 1, or 2;

R² represents a cyclopropyl group, a cyclopropylmethyl group, or a C1-C6alkyl group optionally having one or more halogen atoms;

q is 0, 1, 2, or 3;

R³ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituents selected from Group B, a phenyl group optionallyhaving one or more substituents selected from Group D, a five- orsix-membered aromatic heterocyclic group optionally having one or moresubstituents selected from Group D, a nitro group, OR¹², NR¹¹R¹²,NR^(11a)R^(12a), NR²⁴NR¹¹R¹², NR²⁴OR¹¹, NR¹¹C(O)R¹³, NR²⁴NR¹¹C(O)R¹³,NR¹¹C(O)OR¹⁴, NR²⁴NR¹¹C(O)OR¹⁴, NR¹¹C(O) NR¹⁵R¹⁶, NR²⁴NR¹¹C(O) NR¹⁵R¹⁶,N═CHNR¹⁵R¹⁶, N═S(O)_(x)R¹⁵R¹⁶, S(O)_(y)R¹⁵, C(O)OR¹⁷, C(O)NR¹¹R¹², acyano group, or a halogen atom, and when q is 2 or 3, two or more R³ isidentical to or different from each other;

R¹¹, R¹⁷, R¹⁸, R¹⁹ and R²⁴ represent independently of each other ahydrogen atom, or a C1-C6 chain hydrocarbon group optionally having oneor more halogen atoms;

R¹² represents a hydrogen atom, S(O)₂R²³, a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, or a C1-C6 alkylgroup having one substituent selected from Group F;

R²³ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, or a phenyl group optionally having one or moresubstituents selected from Group D;

R^(11a) and R^(12a) combine together with a nitrogen atom to which theyare attached to form a three- to seven-membered nonaromatic heterocyclicgroup optionally having one or more substituents selected from Group E{wherein said three- to seven-membered nonaromatic heterocyclic grouprepresents an aziridine ring, an azetidine ring, a pyrrolidine ring, animidazoline ring, an imidazolidine ring, a piperidine ring, atetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazinering, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, athiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, athiomorpholine ring, or a 1,4-thiazepane ring};

R¹³ represents a hydrogen atom, a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C3-C7 cycloalkyl groupoptionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3alkyl group optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, or afive- or six-membered aromatic heterocyclic group optionally having oneor more substituents selected from Group D;

R¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a C3-C7 cycloalkyl group optionally having one ormore halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionallyhaving one or more halogen atoms, or a phenyl C1-C3 alkyl group {whereinsaid phenyl moiety of the phenyl C1-C3 alkyl group may optionally haveone or more substituents selected from Group D];

R¹⁵ and R¹⁶ represent independently of each other a C1-C6 alkyl groupoptionally having one or more halogen atoms;

m is 0, 1, or 2;

x is 0 or 1;

y is 0, 1, or 2;

Group B: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, a C3-C6 alkenyloxy group optionally havingone or more halogen atoms, a C3-C6 alkynyloxy group optionally havingone or more halogen atoms, a C1-C6 alkylsulfanyl group optionally havingone or more halogen atoms, a C1-C6 alkylsulfinyl group optionally havingone or more halogen atoms, a C1-C6 alkylsulfonyl group optionally havingone or more halogen atoms, a C3-C6 cycloalkyl group optionally havingone or more halogen atoms, a cyano group, a hydroxy group, and a halogenatom;

Group C: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, and a halogen atom;

Group D: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a hydroxy group, a C1-C6alkoxy group optionally having one or more halogen atoms, a C3-C6alkenyloxy group optionally having one or more halogen atoms, a C3-C6alkynyloxy group optionally having one or more halogen atoms, a sulfanylgroup, a C1-C6 alkylsulfanyl group optionally having one or more halogenatoms, a C1-C6 alkylsulfinyl group optionally having one or more halogenatoms, a C1-C6 alkylsulfonyl group optionally having one or more halogenatoms, an amino group, NHR²¹, NR²¹R²², C(O)R²¹, OC(O)R²¹, C(O)OR²¹, acyano group, a nitro group, and a halogen atom (wherein said R²¹ and R²²represent independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms);

Group E: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, a halogen atom, an oxogroup, a hydroxy group, a cyano group, and a nitro group;

Group F: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, an amino group, NHR²¹, NR²¹R²², a cyanogroup, a phenyl group optionally having one or more substituentsselected from Group D, a five- or six-membered aromatic heterocyclicgroup optionally having one or more substituents selected from Group D,a C3-C7 cycloalkyl group optionally having one or more halogen atoms,and a three- to seven-membered nonaromatic heterocyclic group optionallyhaving one or more substituents selected from Group C {wherein saidthree- to seven-nonaromatic heterocyclic group represents an aziridinering, an azetidine ring, a pyrrolidine ring, an imidazoline ring, animidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, ahexahydropyrimidine ring, a piperazine ring, an azepane ring, anoxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, amorpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, anisothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a1,4-thiazepane ring}]

or an N-oxide compound thereof

(hereinafter, the compound represented by formula (I) or the N-oxidecompound is referred to as “Present compound” or “Compound of thepresent invention”).

[2] The compound according to [1] wherein a combination of A², A³ and A⁴represents a combination where A² represents CR⁶, A³ represents CR⁷, andA⁴ represents CR⁸, a combination where A² represents a nitrogen atom, A³represents CR⁷, and A⁴ represents CR⁸, or a combination where A²represents CR⁶, A³ represents a nitrogen atom, and A⁴ represents CR⁸.[3] The compound according to [1] wherein a combination of A², A³ and A⁴represents a combination wherein A² represents CR⁶, A³ represents CR⁷,and A⁴ represents CR⁸.[4] The compound according to [1] wherein a combination of A², A³ and A⁴represents a combination wherein A² represents a nitrogen atom, A³represents CR⁷, and A⁴ represents CR⁸.[5] The compound according to claim 1 wherein a combination of A², A³and A⁴ represents a combination wherein A² represents CR⁶, A³ representsa nitrogen atom, and A⁴ represents CR⁸.[6] The compound according to any one of [1] to [5] wherein Het¹represents Het¹-1 or Het¹-2.[7] The compound according to any one of [1] to [5] wherein Het¹represents Het¹-3, Het¹-4 or Het¹-5.[8] The compound according to any one of [1] to [5] wherein Het¹represents Het¹-6, or Het¹-7.[9] The compound according to any one of [1] to [5] wherein Het¹represents Het¹-8, or Het¹-9.[10] The compound according to any one of [1] to [9] wherein R³represents a C1-C6 alkyl group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group G, a five membered aromatic heterocyclic groupcontaining one to four nitrogen atoms, a six membered aromaticheterocyclic group containing one to two nitrogen atoms, NR¹¹R¹²,NR²⁴NR¹¹R¹² or a halogen atom,

Group G: a group consisting of a halogen atom and a C1-C6 haloalkylgroup.

[11] The compound according to any one of [1] to [9] wherein R³represents a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom.

[12] The compound according to any one of [1] to [11] wherein R²represents an ethyl group.

[13] The compound according to [1] wherein A¹ represents a nitrogenatom, or CH; a combination of A², A³ and A⁴ represents a combinationwhere A² represents CR⁶, A³ represents CR⁷, and A⁴ represents CR⁸, acombination where A² represents a nitrogen atom, A³ represents CR⁷, andA⁴ represents CR⁸, or a combination where A² represents CR⁶, A³represents a nitrogen atom, and A⁴ represents CR⁸; R¹ represents a C1-C4chain hydrocarbon group having one or more halogen atoms, or a halogenatom; R² represents a methyl group, or an ethyl group; and R³ representsa C1-C6 alkyl group optionally having one or more halogen atoms, aphenyl group optionally having one or more substituents selected fromGroup G, a five membered aromatic heterocyclic group containing one tofour nitrogen atoms (wherein said five membered aromatic heterocyclicgroup may optionally have one or more substituents selected from GroupG), a six membered aromatic heterocyclic group containing one to twonitrogen atoms (wherein said six membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group G),NR¹¹R¹², NR²⁴NR¹¹R¹², or a halogen atom; R¹¹, R¹² and R²⁴ representindependently of each other a hydrogen atom, a C1-C3 alkyl groupoptionally having one or more halogen atoms; R⁶, R⁷ and R⁸ representindependently of each other a C1-C6 alkyl group optionally having one ormore halogen atoms, or a halogen atom; Het¹ represents Het¹-1 or Het¹-2;and q is 0 or 1;

Group G: a group consisting of a halogen atom and a C1-C6 haloalkylgroup.

[14] The compound according to [1] wherein A¹ represents a nitrogenatom, or CH; a combination of A², A³ and A⁴ represents a combinationwhere A² represents CR⁶, A³ represents CR⁷, and A⁴ represents CR⁸, acombination where A² represents a nitrogen atom, A³ represents CR⁷, andA⁴ represents CR⁸, or a combination where A² represents CR⁶, A³represents a nitrogen atom, and A⁴ represents CR⁸; R¹ represents a C1-C4chain hydrocarbon group having one or more halogen atoms, or a halogenatom; R² represents a methyl group, or an ethyl group; R³ represents aC1-C6 alkyl group optionally having one or more halogen atoms, a phenylgroup optionally having one or more substituents selected from Group G,a five membered aromatic heterocyclic group containing one to fournitrogen atoms (wherein said five membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group G), asix membered aromatic heterocyclic group containing one to two nitrogenatoms (wherein said six membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group G),NR¹¹R¹², NR²⁴NR¹¹R¹², or a halogen atom; R¹¹, R¹², and R²⁴ representindependently of each other a hydrogen atom, a C1-C3 alkyl groupoptionally having one or more halogen atoms; R⁶, R⁷ and R⁸ representindependently of each other a hydrogen atom, a C1-C6 alkyl groupoptionally having one or more halogen atoms, or a halogen atom; and Het¹represents Het¹-1 or Het¹-2; and q is 0 or 1;

Group G: a group consisting of a halogen atom and a C1-C6 haloalkylgroup.

[15] The compound according to [1] wherein A¹ represents a nitrogenatom, or CH; a combination of A², A³, and A⁴ represents a combinationwhere A² represents CH, A³ represents CH, and A⁴ represents CH, acombination where A² represents a nitrogen atom, A³ represents CH, andA⁴ represents CH, a combination where A² represents CH, A³ represents anitrogen atom, and A⁴ represents CH; R¹ represents a C1-C4 chainhydrocarbon group having one or more halogen atoms, or a halogen atom;R² represents an ethyl group; q is 0 or 1; R³ represents a C1-C6 alkylgroup optionally having one or more halogen atoms, or a halogen atom;and Het¹ represents Het¹-1.[16] A composition for controlling a harmful arthropod comprising thecompound according to any one of [1] to [15] and an inert carrier.[17] A method for controlling a harmful arthropod, said methodcomprising applying an effective amount of the compound according to anyone of [1] to [15] to a harmful arthropod or a habitat where a harmfularthropod lives.[18] A composition comprising one or more ingredients selected from thegroup consisting of the following Group (a), Group (b), Group (c), andGroup (d), and the compound according to any one of [1] to [14],

Group (a): one or more ingredients selected from the group consisting ofinsecticidal ingredients, miticidal ingredients, and nematicidalingredients;

Group (b): fungicidal ingredients;

Group (c): plant growth modulating ingredients; and

Group (d): phytotoxicity-reducing ingredients.

Effect of Invention

The compound of the present invention has an excellent efficacy oncontrolling harmful arthropods, and is thus useful as an activeingredient for an agent for controlling harmful arthropod.

MODE FOR CARRYING OUT THE INVENTION

The substituent(s) as described herein is/are explained.

The term of “optionally having one or more halogen atoms” or “mayoptionally have one or more halogen atoms” means that when two or morehalogen atoms is present, these halogen atoms may be identical to ordifferent from each other.

The expression of “CX—CY” as used herein represents that the number ofcarbon atom is from X to Y. For example, the expression of “C1-C6”represents that the number of carbon atom is from 1 to 6.

The term “halogen atom” represents fluorine atom, chlorine atom, bromineatom, or iodine atom.

The term of “chain hydrocarbon group” represents an alkyl group, analkenyl group, or an alkynyl group.

Example of the term of “alkyl group” include methyl group, ethyl group,propyl group, isopropyl group, 1,1-dimethylpropyl group,1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butylgroup, pentyl group, and hexyl group.

Example of the term of “alkenyl group” include vinyl group, 1-propenylgroup, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenylgroup, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group,3-butenyl group, 4-pentenyl group, and 5-hexenyl group.

Example of the term of “alkynyl group” includes ethynyl group,1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group,1,1-dimethyl-2-propynyl group, 4-pentynyl group, and 5-hexynyl group.

The term of “C1-C6 haloalkyl group” represents a group wherein hydrogenatom(s) is/are replaced with halogen atom(s), and includes, for example,a C1-C6 fluoroalkyl group.

Example of the term of “C1-C6 haloalkyl group” include chloroethylgroup, 2,2,2-trifluoroethyl group, 2-bromo-1,1,2,2-tetrafluoroethylgroup, 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, and perfluorohexyl group.

Examples of the term of “C1-C6 fluoroalkyl group” include2,2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, and perfluorohexyl group.

Example of the term of “cycloalkyl group” includes cyclopropyl group,cyclobutyl group, cyclopentyl group, cyclohexyl group and cycloheptylgroup.

Examples of the term of “three- to seven-membered nonaromaticheterocyclic group” include aziridine ring, azetidine ring, pyrrolidinering, imidazoline ring, imidazolidine ring, piperidine ring,tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring,azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring,morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidinering, 1,3-thiazinane ring, thiomorpholine ring, or 1,4-thiazepane ring.Examples of the three to seven membered nonaromatic heterocyclic groupoptionally having one or more substituents selected from Group E includethe followings:

Examples of the term of “phenyl C1-C3 alkyl group {the phenyl moiety inthe phenyl C1-C3 alkyl group may optionally have one or moresubstituents selected from Group D}” include benzyl group,2-fluorobenzyl group, 4-chlorobenzyl group, 4-(trifluoromethyl)benzylgroup, and 2-[4-(trifluoromethyl)phenyl]ethyl group.

The term of “(C3-C6 cycloalkyl)C1-C3 alkyl group optionally having oneor more halogen atoms” represents a group wherein the (C3-C6 cycloalkyl)and/or the (C1-C3 alkyl) may optionally has/have one or more halogenatoms, and includes, for example, (2,2-difluorocyclopropyl)methyl group,2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group.

The term of “five- or six-membered aromatic heterocyclic group”represents a five membered aromatic heterocyclic group or a six memberedaromatic heterocyclic group. Examples of the five membered aromaticheterocyclic group include pyrrolyl group, furyl group, thienyl group,pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group,oxazolyl group, isoxazolyl group, thiazolyl group, oxadiazolyl group,and thiadiazolyl group. As the five membered aromatic heterocyclicgroup, a five membered aromatic heterocyclic group containing 1 to 4nitrogen atoms, that is, pyrrolyl group, pyrazolyl group, imidazolylgroup, 1,2,4-triazolyl group, 1,2,3-triazolyl group, or tetrazolyl groupis preferably included. Examples of the six membered aromaticheterocyclic group include pyridyl group, pyridazinyl group, pyrimidinylgroup, and pyrazinyl group. As the six membered aromatic heterocyclicgroup, a six membered aromatic heterocyclic group containing one to twonitrogen atoms, that is, pyridyl group, pyridazinyl group, pyrimidinylgroup, and pyrazinyl group is preferably included.

In the compound of the present invention, the structure represented bythe following formula:

(hereinafter, the formula is referred to as Het². In the formula, #¹represents a binding position to the Het¹, and #² represents a bindingposition to the following formula:

represents the following formulae: Het²-1, Het²-2, Het²-3, or Het²-4:

(wherein the symbols are the same as defined above.).

An N-oxide compound represents a compound represented by formula (N-1),a compound represented by formula (N-2), a compound represented byformula (N-3), a compound represented by formula (N-4), a compoundrepresented by formula (N-5), or a compound represented by formula(N-6):

[wherein A⁵ represents a nitrogen atom, N⁺O⁻, or CR⁹, and the othersymbols are the same as defined above.]).

Examples of the embodiment of the compound of the present inventioninclude the following compounds.

Embodiment 1

A compound of the present invention wherein R¹ represents a C1-C4 chainhydrocarbon group having one or more halogen atoms, or a halogen atom;

Embodiment 2

A compound of the present invention wherein R¹ represents a C1-C4 alkylgroup having three or more fluorine atoms;

Embodiment 3

A compound of the present invention wherein R² represents a cyclopropylgroup, a cyclopropylmethyl group, or a C1-C3 alkyl group optionallyhaving one or more halogen atoms;

Embodiment 4

A compound of the present invention wherein R² represents a methylgroup, an ethyl group, a cyclopropyl group, or a cyclopropylmethylgroup;

Embodiment 5

A compound of the present invention wherein R² represents a methyl groupor an ethyl group;

Embodiment 6

A compound of the present invention wherein R² represents an ethylgroup;

Embodiment 7

A compound of the present invention wherein R³ represents a C1-C6 chainhydrocarbon group optionally having one or more substituents selectedfrom Group B, a phenyl group optionally having one or more substituentsselected from Group D, or a six membered aromatic heterocyclic groupselected from Group V (wherein said six membered aromatic heterocyclicgroup may optionally have one or more substituents selected from GroupD), a five membered aromatic heterocyclic group selected from Group W(wherein said five membered aromatic heterocyclic group may optionallyhave one or more substituents selected from Group D), OR¹², NR¹¹R¹²,NR^(11a)R^(12a), NR²⁴NR¹¹R¹², or a halogen atom;

Group V:

Group W:

{In the above structure formula, R²⁶ represents a C1-C6 alkyl groupoptionally having one or more halogen atoms.).

Embodiment 8

A compound of the present invention wherein R³ represents a C1-C6 alkylgroup optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group G, a sixmembered aromatic heterocyclic group selected from Group V (wherein saidsix membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group G), a five membered aromaticheterocyclic group selected from W-1 to W-6 (wherein said five memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group G), NR¹¹R¹², NR²⁴NR¹¹R¹², or a halogen atom, R¹¹,R¹², and R²⁴ represent independently of each other a hydrogen atom, or aC1-C3 alkyl group optionally having one or more halogen atoms;

Embodiment 9

A compound of the present invention wherein R³ represents a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom;

Embodiment 10

A compound of the present invention wherein R³ represents a C1-C6 alkylgroup having one or more halogen atoms;

Embodiment 11

A compound of the present invention wherein R⁶ represents a hydrogenatom, a C1-C6 alkyl group optionally having one or more halogen atoms,or a halogen atom;

Embodiment 12

A compound of the present invention wherein q is 0 or 1;

Embodiment 13

A compound of the present invention wherein q is 0;

Embodiment 14

A compound of the present invention wherein A¹ represents a nitrogenatom, or CR⁹, and R⁹ represents a hydrogen atom, or a halogen atom;

Embodiment 15

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH;

Embodiment 16

A compound of the present invention wherein A¹ represents a nitrogenatom;

Embodiment 17

A compound of the present invention wherein Het¹ represents Het¹-1,Het¹-2, Het¹-3, Het¹-4, or Het¹-5:

Embodiment 18

A compound of the present invention wherein Het¹ represents Het¹-1, orHet¹-2;

Embodiment 19

A compound of the present invention wherein Het¹ represents Het¹-1;

Embodiment 20

A compound of the present invention wherein Het¹ represents Het¹-2;

Embodiment 21

A compound of the present invention wherein Het¹ represents Het¹-5;

Embodiment 22

A compound of the present invention wherein Het² represents Het²-1,Het²-2, or Het²-3;

Embodiment 23

A compound of the present invention wherein Het² represents Het²-1;

Embodiment 24

A compound of the present invention wherein Het² represents Het²-2;

Embodiment 25

A compound of the present invention wherein Het² represents Het²-3;

Embodiment 26

A compound of the present invention wherein Het² represents Het²-4;

Embodiment 27

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH, R¹ represents a C1-C4 chain hydrocarbon group having one ormore halogen atoms, or a halogen atom, R² represents a cyclopropylgroup, a cyclopropylmethyl group, or a C1-C3 alkyl group optionallyhaving one or more halogen atoms, R³ represents a C1-C6 chainhydrocarbon group optionally having one or more substituents selectedfrom Group B, a phenyl group optionally having one or more substituentsselected from Group D, a six membered aromatic heterocyclic groupselected from Group V (wherein said six membered aromatic heterocyclicgroup may optionally have one or more substituents selected from GroupD), a five membered aromatic heterocyclic group selected from Group W(wherein said five membered aromatic heterocyclic group may optionallyhave one or more substituents selected from Group D), OR¹², NR¹¹R¹²,NR^(11a)R^(12a), NR²⁴NR¹¹R¹², or a halogen atom, and R⁶, R⁷ and R⁸represent independently of each other a hydrogen atom, a C1-C6 alkylgroup optionally having one or more halogen atoms, or a halogen atom;

Embodiment 28

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH, R¹ represents a C1-C4 alkyl group having three or morefluorine atoms, R² represents a cyclopropyl group, a cyclopropylmethylgroup, or a C1-C3 alkyl group optionally having one or more halogenatoms, R³ represents a C1-C6 chain hydrocarbon group optionally havingone or more substituents selected from Group B, a phenyl groupoptionally having one or more substituents selected from Group D, a sixmembered aromatic heterocyclic group selected from Group V (wherein saidsix membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group D), a five membered aromaticheterocyclic group selected from Group W (wherein said five memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group D), OR¹², NR¹¹R¹², NR^(11a)R^(12a), NR²⁴NR¹¹R¹², ora halogen atom, and R⁶, R⁷ and R⁸ represent independently of each othera hydrogen atom, a C1-C6 alkyl group optionally having one or morehalogen atoms, or a halogen atom;

Embodiment 29

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH; R¹ represents a C1-C4 alkyl group having three or morefluorine atoms, R² represents a methyl group, or an ethyl group, R³represents a C1-C6 alkyl group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group G, a six membered aromatic heterocyclic groupselected from Group V (wherein said six membered aromatic heterocyclicgroup may optionally have one or more substituents selected from GroupG), a five membered aromatic heterocyclic group selected from W-1 to W-6(wherein said five membered aromatic heterocyclic group may optionallyhave one or more substituents selected from Group G), NR¹¹R¹²,NR²⁴NR¹¹R¹², or a halogen atom, R¹¹, R¹² and R²⁴ represent independentlyof each other a hydrogen atom, or a C1-C3 alkyl group optionally havingone or more halogen atoms, and R⁶, R⁷ and R⁸ represent independently ofeach other a hydrogen atom, a C1-C6 alkyl group optionally having one ormore halogen atoms, or a halogen atom;

Embodiment 30

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH, R¹ represents a C1-C4 alkyl group having three or morefluorine atoms, R² represents an ethyl group, R³ represents a C1-C6chain hydrocarbon group optionally having one or more halogen atoms, ora halogen atom, and R⁶, R⁷ and R⁸ represent independently of each othera C1-C6 alkyl group optionally having one or more halogen atoms, or ahalogen atom;

Embodiment 31

A compound of the present invention wherein A¹ represents a nitrogenatom, R¹ represents a C1-C4 alkyl group having three or more fluorineatoms, R² represents an ethyl group, R³ represents a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom, and R⁶, R⁷ and R⁸ represent independently of each other ahydrogen atom, a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom;

Embodiment 32

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH, R¹ represents a C1-C4 alkyl group having three or morefluorine atoms, R² represents an ethyl group, R³ represents a C1-C6chain hydrocarbon group optionally having one or more substituentsselected from Group B, a phenyl group optionally having one or moresubstituents selected from Group D, a six membered aromatic heterocyclicgroup selected from Group V (wherein said six membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a five membered aromatic heterocyclic group selected fromGroup W (wherein said five membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), OR¹²,NR¹¹R¹², NR^(11a)R^(12a), NR²⁴NR¹¹R¹², or a halogen atom, and R⁶, R⁷ andR⁸ represent independently of each other a hydrogen atom, a C1-C6 alkylgroup optionally having one or more halogen atoms, or a halogen atom;

Embodiment 33

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH, R¹ represents a C1-C4 alkyl group having three or morefluorine atoms, R² represents an ethyl group, R³ represents a C1-C6alkyl group optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group G, a sixmembered aromatic heterocyclic group selected from Group V (wherein saidsix membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group G), a five membered aromaticheterocyclic group selected from W-1 to W-6 (wherein said five memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group G), NR¹¹R¹², NR²⁴NR¹¹R¹², or a halogen atom, R¹¹,R¹² and R²⁴ represent independently of each other a hydrogen atom, or aC1-C3 alkyl group optionally having one or more halogen atoms, and R⁶,R⁷ and R⁸ represent independently of each other a hydrogen atom, a C1-C6alkyl group optionally having one or more halogen atoms, or a halogenatom;

Embodiment 34

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, andHet² represents Het²-1, Het²-2, or Het²-3;

Embodiment 35

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, andHet² represents Het²-1;

Embodiment 36

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, andHet² represents Het²-2;

Embodiment 37

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, andHet² represents Het²-3;

Embodiment 38

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, andHet² represents Het²-4;

Embodiment 39

The compound described in any one of [Embodiment 27] to [Embodiment 32]wherein Het¹ represents Het¹-1, and Het² represents Het²-1, Het²-2, orHet²-3;

Embodiment 40

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, and Het² represents Het²-1;

Embodiment 41

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, and Het² represents Het²-2;

Embodiment 42

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, and Het² represents Het²-3;

Embodiment 43

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-1, and Het² represents Het²-4;

Embodiment 44

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-2, and Het² represents Het²-1, Het²-2, orHet²-3;

Embodiment 45

The compound described in any one of [Embodiment 27] to [Embodiment 33)wherein Het¹ represents Het¹-2, and Het² represents Het²-1;

Embodiment 46

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-2, and Het² represents Het²-2;

Embodiment 47

The compound described in any one of [Embodiment 27] to (Embodiment 33]wherein Het¹ represents Het¹-2, and Het² represents Het²-3;

Embodiment 48

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-2, and Het² represents Het²-4;

Embodiment 49

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-5, and Het² represents Het²-1, Het²-2 orHet²-3, and R¹ represents a C1-C4 chain hydrocarbon group optionallyhaving one or more halogen atoms, or a halogen atom;

Embodiment 50

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-5, Het² represents Het²-1, and R^(1a)represents a C1-C4 chain hydrocarbon group optionally having one or morehalogen atoms, or a halogen atom;

Embodiment 51

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-5, Het² represents Het²-2, and R^(1a)represents a C1-C4 chain hydrocarbon group optionally having one or morehalogen atoms, or a halogen atom;

Embodiment 52

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-5, Het² represents Het²-3, and R^(1a)represents a C1-C4 chain hydrocarbon group optionally having one or morehalogen atoms, or a halogen atom;

Embodiment 53

The compound described in any one of [Embodiment 27] to [Embodiment 33]wherein Het¹ represents Het¹-5, Het² represents Het²-4, and R^(1a)represents a C1-C4 chain hydrocarbon group optionally having one or morehalogen atoms, or a halogen atom;

Embodiment 54

A compound of the present invention wherein A¹ represents a nitrogenatom, R¹ represents a C1-C4 chain hydrocarbon group having one or morehalogen atoms, or a halogen atom, R² represents an ethyl group, R³represents a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom, Het¹ represents Het¹-1, Het² representsHet²-1, Het²-2, or Het²-3, and R⁶, R⁷ and R⁸ represent a hydrogen atom,and q is 0 or 1;

Embodiment 55

The compound described in [Embodiment 54] wherein Het² representsHet²-1;

Embodiment 56

The compound described in [Embodiment 54] wherein Het² representsHet²-2;

Embodiment 57

The compound described in [Embodiment 54] wherein Het² representsHet²-3;

Embodiment 58

The compound described in [Embodiment 55] wherein X¹ represents CH, X³represents CR³², X⁴ represents CR³³, and X⁵ represents CH;

Embodiment 59

The compound described in [Embodiment 55] wherein X¹ represents anitrogen atom, X³ represents CR³², X⁴ represents CR³³, and X⁵ representsCH;

Embodiment 60

The compound described in [Embodiment 55] wherein X¹ represents CH, X³represents a nitrogen atom, X⁴ represents CR³³, and X⁵ represents CH;

Embodiment 61

The compound described in [Embodiment 55] wherein X¹ represents CH, X³represents CR³², X⁴ represents a nitrogen atom, and X⁵ represents CH;

Embodiment 62

The compound described in [Embodiment 55] wherein X¹ represents CH, X³represents CR, X⁴ represents CR³³, and X⁵ represents a nitrogen atom;

Embodiment 63

The compound described in [Embodiment 56] wherein X¹ represents CH, X³represents CR³², X⁴ represents CR³³, and X⁵ represents CH;

Embodiment 64

The compound described in [Embodiment 56] wherein X¹ represents anitrogen atom, X³ represents CR³², X⁴ represents CR³³, and X⁵ representsCH;

Embodiment 65

The compound described in [Embodiment 56] wherein X¹ represents CH, X³represents a nitrogen atom, X⁴ represents CR³³, and X⁵ represents CH;

Embodiment 66

The compound described in [Embodiment 56] wherein X¹ represents CH, X³represents CR³², X⁴ represents a nitrogen atom, and X⁵ represents CH;

Embodiment 67

The compound described in [Embodiment 56] wherein X¹ represents CH, X³represents CR, X⁴ represents CR³³, and X⁵ represents a nitrogen atom;

Embodiment 68

The compound described in [Embodiment 57] wherein X¹ represents CH, X³represents CR³², X⁴ represents CR³³, and X⁵ represents CH;

Embodiment 69

The compound described in [Embodiment 57] wherein X¹ represents anitrogen atom, X³ represents CR³², X⁴ represents CR³³, and X⁵ representsCH;

Embodiment 70

The compound described in [Embodiment 57] wherein X¹ represents CH, X³represents a nitrogen atom, X⁴ represents CR³³, and X⁵ represents CH;

Embodiment 71

The compound described in [Embodiment 57] wherein X¹ represents CH, X³represents CR³², X⁴ represents a nitrogen atom, and X⁵ represents CH;

Embodiment 72

The compound described in [Embodiment 57] wherein X¹ represents CH, X³represents CR³², X⁴ represents CR³³, and X⁵ represents a nitrogen atom;

Embodiment 73

A compound represented by formula (I-1):

[wherein, any one of R⁵¹, R⁵² and R⁵³ represents a C1-C4 chainhydrocarbon group having one or more halogen atoms, and the remaininggroups represent a hydrogen atom or a halogen atom.];

Embodiment 74

A compound represented by formula (I-2):

[wherein, any one of R⁵⁵, R⁵⁶ and R⁵⁷ represents OR⁴, a C1-C4 chainhydrocarbon group having one or more halogen atoms, or a halogen atom,the remaining groups represent a hydrogen atom, or a halogen atom, andR⁵⁴ represents a hydrogen atom, a halogen atom, or a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms.];

Embodiment 75

A compound represented by formula (I-3):

[wherein, R⁵⁸ represents a halogen atom, or a C1-C4 chain hydrocarbongroup having one or more halogen atoms.];

Embodiment 76

A compound represented by formula (I-4):

[wherein, R⁵⁹ represents a halogen atom, or a C1-C4 chain hydrocarbongroup having one or more halogen atoms.];

Embodiment 77

A compound represented by formula (I-5):

[wherein, any one of R⁶⁰ and R⁶¹ represents a halogen atom, or a C1-C4chain hydrocarbon group having one or more halogen atoms, and the otherrepresents a hydrogen atom, a halogen atom, or a C1-C4 chain hydrocarbongroup having one or more halogen atoms.];

Embodiment 78

A compound of the present invention wherein R⁶, R⁷ and R⁸ represents ahydrogen atom, a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom;

Embodiment 79

A compound of the present invention wherein A¹ represents a nitrogenatom, or CH, R¹ represents a C1-C4 alkyl group having three or morefluorine atoms, R² represents an ethyl group, R³ represents a C1-C6chain hydrocarbon group optionally having one or more halogen atoms, ora halogen atom, and R⁶, R⁷ and R⁸ represent independently of each othera hydrogen atom, a C1-C6 alkyl group optionally having one or morehalogen atoms, or a halogen atom;

Embodiment 80

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, and Het² represents Het²-1,Het²-2, or Het²-3;

Embodiment 81

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, and Het² represents Het²-1;

Embodiment 82

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, and Het² represents Het²-2;

Embodiment 83

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, and Het² represents Het²-3;

Embodiment 84

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, Het¹-2, Het¹-3, Het¹-4, or Het¹-5, and Het² represents Het²-4;

Embodiment 85

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, and Het² represents Het²-1, Het²-2, or Het²-3;

Embodiment 86

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, and Het² represents Het²-1;

Embodiment 87

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, and Het² represents Het²-2;

Embodiment 88

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, and Het² represents Het²-3;

Embodiment 89

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-1, and Het² represents Het²-4;

Embodiment 90

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-2, and Het² represents Het²-1, Het²-2, or Het²-3;

Embodiment 91

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-2, and Het² represents Het²-1;

Embodiment 92

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-2, and Het² represents Het²-2;

Embodiment 93

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-2, and Het² represents Het²-3;

Embodiment 94

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-2, and Het² represents Het²-4;

Embodiment 95

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-5, Het² represents Het²-1, Het²-2, or Het²-3, and R^(1a) representsa C1-C4 chain hydrocarbon group optionally having one or more halogenatoms, or a halogen atom;

Embodiment 96

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-5, Het² represents Het²-1, and R^(1a) represents a C1-C4 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom;

Embodiment 97

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-5, Het² represents Het²-2, and R^(1a) represents a C1-C4 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom;

Embodiment 98

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-5, Het² represents Het²-3, and R^(1a) represents a C1-C4 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom;

Embodiment 99

The compound described in [Embodiment 79] wherein Het¹ representsHet¹-5, Het² represents Het²-4, and R^(1a) represents a C1-C4 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom.

Next, a process for preparing the compound of the present invention isexplained.

The compounds of the present invention and the production intermediatecompounds can be prepared by the below-mentioned processes.

Process 1

In the compound of the present invention, a compound wherein n is 1(hereinafter, referred to as Compound (1-n1)) or a compound wherein n is2 (hereinafter, referred to as Compound (1-n2)) may be prepared byoxidizing a compound wherein n is 0 (hereinafter, referred to asCompound (1-n0)).

[wherein, the symbols are the same as defined above.]

First, a process for preparing the Compound (1-n1) from the Compound(1-n0) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated aliphatichydrocarbons such as dichloromethane and chloroform (hereinafter,collectively referred to as halogenated aliphatic hydrocarbons);nitriles such as acetonitrile (hereinafter, collectively referred tonitriles); alcohols such as methanol and ethanol (hereinafter,collectively referred to as alcohols); acetic acid; water; and mixedsolvents thereof.

Examples of the oxidizing agent to be used in the reaction includesodium periodate, m-chloroperoxybenzoic acid (hereinafter, referred toas mCPBA) and hydrogen peroxide. When hydrogen peroxide is used as anoxidizing agent, sodium carbonate or a catalyst may be added as needed.

Examples of the catalyst to be used in the reaction include tungsticacid, and sodium tungstate.

In the reaction, the oxidizing agent is used usually within a range of 1to 1.2 molar ratio(s), the base is used usually within a range of 0.01to 1 molar ratio(s), and the catalyst is used usually within a range of0.01 to 0.5 molar ratios, as opposed to 1 mole of the compound (1-n0).

The reaction temperature of the reaction is usually within a range of−20 to 80° C. The reaction period of the reaction is usually within arange of 0.1 to 12 hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvent(s), and ifnecessary, the organic layers are washed with an aqueous solution of areducing agent (such as sodium sulfite, and sodium thiosulfate) and anaqueous solution of a base (such as sodium hydrogen carbonate). Theresulting organic layers are dried and concentrated to give the compound(1-n1).

Next, a process for preparing the compound (1-n2) from the compound(1-n1) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated aliphatichydrocarbons, nitriles, alcohols, acetic acid, water, and mixed solventsthereof.

Examples of the oxidizing agent to be used in the reaction include mCPBAand peroxide hydrogen. When peroxide hydrogen is used as an oxidizingagent, a base or a catalyst may be added as needed.

Examples of the base to be used in the reaction include sodiumcarbonate.

Examples of the catalyst to be used in the reaction include sodiumtungstate.

In the reaction, the oxidizing agent is used usually within a range of 1to 2 molar ratio(s), the base is used usually within a range of 0.01 to1 molar ratio(s), and the catalyst is used usually within a range of0.01 to 0.5 molar ratios, as opposed to 1 mole of the compound (1-n1).

The reaction temperature of the reaction is usually within a range of−20 to 120° C. The reaction period of the reaction is usually within arange of 0.1 to 12 hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvent(s), and ifnecessary, the organic layers are washed with an aqueous solution of areducing agent (such as sodium sulfite, and sodium thiosulfate) and anaqueous solution of a base (such as sodium hydrogen carbonate). Theresulting organic layers are dried and concentrated to give the compound(1-n2).

Also, the compound (1-n2) may be prepared by reacting the compound(1-n0) with an oxidizing agent in one step (one pot).

The reaction may be carried out by using the oxidizing agent in a ratioof usually 2 to 5 molar ratios as opposed to 1 mole of the compound(1-n0) according to the method for preparing the compound (1-n2) fromthe compound (1-n1).

Process 2

The compound (1-n0) may be prepared by reacting a compound representedby formula (M-1) (hereinafter, referred to as Compound (M-1)) and acompound represented by formula (R-1) (hereinafter, referred to asCompound (R-1)) in the presence of a base.

[wherein, X¹⁰ represents a halogen atom, and the other symbols are thesame as defined above.]

The reaction is usually carried out in the presence of a solvent.Examples of the solvents to be used in the reaction include ethers suchas tetrahydrofuran (hereinafter, referred to as THF), and ethyleneglycol dimethyl ether (hereinafter, referred to as DME), methyltert-butyl ether, and 1,4-dioxane (hereinafter, collectively referred toas ethers); aromatic hydrocarbons such as toluene and xylene(hereinafter, collectively referred to as aromatic hydrocarbons);nitriles; and aprotic polar solvents such as dimethylformamide(hereinafter, referred to as DMF), N-methylpyrrolidone, and dimethylsulfoxide (hereinafter, collectively referred to as polar aproticsolvent); and mixed solvents thereof.

Examples of the base to be used in the reaction include alkali metalcarbonates such as sodium carbonate and potassium carbonate(hereinafter, collectively referred to as alkali metal carbonates); andalkali metal hydrides such as sodium hydride (hereinafter, collectivelyreferred to as alkali metal hydrides).

In the reaction, the compound (R-1) is used usually within a range of 1to 10 molar ratio(s), and the base is used usually within a range of 1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-1).

The reaction temperature of the reaction is usually within a range of−20 to 150° C. The reaction period of the reaction is usually within arange of 0.5 to 24 hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvent(s), and theorganic layers are worked up (for example, drying and concentration) togive the compound (1-n0).

In the reaction, X¹⁰ is preferably a fluorine atom or a chlorine atom.

Process 3

A compound represented by formula (1a) (hereinafter, referred toCompound (1a)) may be prepared by reacting a compound represented byformula (M-3) (hereinafter, referred to as Compound (M-3)) with acompound represented by formula (R-2) (hereinafter, referred to asCompound (M-3)) in the presence of a metal catalyst.

[wherein, X¹¹ represents a bromine atom, or an iodine atom; X¹²represents a chlorine atom, a bromine atom, or an iodine atom; Mrepresents 9-borabiclo[3.3.1]nonan-9-yl, —B(OH)₂, a4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl, Sn(n-C₄H₉)₃, ZnCl, MgCl,or MgBr; Het¹⁰ represents Het¹-1, Het¹-2, Het¹-6, Het¹-7, Het¹-8, orHet¹-9; and the other symbols are the same as defined above.]

First, the process for preparing the compound (1a) from the compound(M-3) and the compound (R-2) is described.

The reaction is usually carried out in the presence of a solvent.Examples of the solvent to be used in the reaction include ethers,aromatic hydrocarbons, aprotic polar solvents, water, and mixed solventsthereof.

Examples of the metal catalyst to be used in the reaction includepalladium catalysts such as tetrakis(triphenylphosphine)palladium(0),1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride,tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate;nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II)chloride; and copper catalyst such as copper(I) iodide and copper(I)chloride.

A ligand, a base, or an inorganic halogenated compound may be added tothe reaction as needed.

Examples of the ligand to be used in the reaction includetriphenylphosphine, Xantphos,2,2′-bis(diphenylphoshino)-1,1′-binaphthyl,1,1′-bis(diphenylphoshino)ferrocene,2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl,2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl,1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol,8-hydroquinoline, and 1,10-phenanthroline.

Examples of the base to be used in the reaction include alkali metalhydrides; alkali metal carbonates; and organic bases.

Examples of the inorganic halogenated compounds include alkali metalfluorides such as potassium fluoride, and sodium fluoride; and alkalimetal chlorides such as lithium chloride, and sodium chloride.

In the reaction, the compound (M-3) is usually used within a range of 1to 10 molar ratio(s), the metal catalyst is usually used within a rangeof 0.01 to 0.5 molar ratios, the ligand is usually used within a rangeof 0.01 to 1 molar ratio(s), the base is usually used within a range of0.1 to 5 molar ratio(s), and the inorganic halogenated compound isusually used within a range of 0.1 to 5 molar ratios, as opposed to 1mole of the compound (R-2).

The reaction temperature is usually within a range of −20 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, water is added to the reaction mixtures,and the reaction mixtures are extracted with organic solvent(s), and theorganic layers are worked up (for example, drying and concentration) togive the compound (1a).

The compound (R-2) is a commercially available compound, or can beprepared by using a known method.

The compound (M-3) may be prepared by using a compound represented byformula (M-2) (hereinafter, referred to as Compound (M-2)) according tothe method described in WO 06/097691 or the method described in TheJournal Of Organic Chemistry, 1995, 60, 7508-7510.

Process 4

A compound represented by formula (1b) (hereinafter, referred to asCompound (1b)) may be prepared by reacting a compound represented byformula (M-4) (hereinafter, referred to as Compound (M-4)) with acompound represented by formula (R-3) (hereinafter, referred to asCompound (R-3)) in the presence of a base. A compound represented byformula (1c) (hereinafter, referred to as Compound (1c)) may be preparedby reacting the compound (M-4) with a compound represented by formula(R-4) (hereinafter, referred to as Compound (R-4)) in the presence of abase. A compound represented by formula (1d) (hereinafter, referred toas Compound (1d)) may be prepared by reacting the compound (M-4) with acompound represented by formula (R-5) (hereinafter, referred to asCompound (R-5)) in the presence of a base.

[wherein, X¹³ represents a chlorine atom, or a fluorine atom; and theother symbols are the same as defined above.]

First, a process for preparing the compound (1b) from the compound (M-4)and the compound (R-3) is described.

The compound (R-3) is a commercially available compound, or can beprepared by using a known method.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, polar aprotic solvent, and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates, and alkali metal hydrides.

In the reaction, the compound (R-3) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used with a range of 1 to10 molar ratios, as opposed to 1 mole of the compound (M-4).

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvent(s), and theorganic layers are worked up (for example, drying and concentration) togive the compound (1b).

The compound (1c) may be prepared by using the compound (R-4) in theplace of the compound (R-3).

The compound (R-4) is a commercially available compound, or can beprepared by using a known method.

The compound (1d) may be prepared by using the compound (R-5) in theplace of the compound (R-3) according to the method of preparing thecompound (1b).

The compound (R-5) is a commercially available compound, or can beprepared by using a known method.

Process 5

The compound (1a) may be prepared by reacting a compound represented byformula (M-14) (hereinafter, referred to as Compound (M-14)) with thecompound (R-2).

[wherein, R⁵⁰ represents a C1-C10 chain hydrocarbon group having one ormore halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one ormore halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having oneor more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group havingone or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group havingone or more substituents selected from Group G, or a C3-C7 cycloalkylgroup having one or more substituents selected from Group G; and theother symbols are the same as defined above.]

The reaction may be conducted according to the method described inProcess 3 for preparing the compound (1a) from the compound (M-3) andthe compound (R-2).

A process for an intermediate compound is described below.

Reference Process 1

The compound (M-2) and the compound (M-4) may be prepared according tothe below-mentioned scheme to prepare them as a compound represented byformula (M-6) (hereinafter, referred to as Compound (M-6)) or a compoundrepresented by formula (M-7) (hereinafter, referred to as Compound(M-7)).

[wherein, X¹⁴ represents a chlorine atom, or a bromine atom, X¹⁵represents a fluorine atom or an iodine atom; and the other symbols arethe same as defined above.]

First, a process for preparing the compound (M-6) from the compound(M-5) is described.

The compound (M-6) may be prepared by reacting the compound (M-5) withphosphorus oxychloride or phosphorus oxybromide.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include aromatic hydrocarbons.

When phosphorus oxychloride is used, phosphorus oxychloride may be usedas a solvent.

In the reaction, phosphorus oxychloride or phosphorus oxybromide isusually used within a range of 1 to 10 molar ratio(s) as opposed to 1mole of the compound (M-5).

The reaction temperature is usually within a range of 0 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvents, and theorganic layers are worked up (for example, drying and concentration) togive the compound (M-6).

Next, a process for preparing the compound (M-7) from the compound (M-6)is described.

The compound (M-7) may be prepared by reacting the compound (M-6) withinorganic fluoride or inorganic iodide.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include nitriles, polar aproticsolvent, nitrogen-containing aromatic solvents, and mixed solventsthereof.

Examples of the inorganic fluoride compound to be used in the reactioninclude potassium fluoride, sodium fluoride and cesium fluoride.Examples of the inorganic iodide compound to be used in the reactioninclude potassium iodide and sodium iodide.

In the reaction, inorganic fluoride compound or inorganic iodidecompound is usually used within a range of 1 to 10 molar ratio(s) asopposed to 1 mole of the compound (M-6).

The reaction temperature is usually within a range of 0 to 250° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvents, and theorganic layers are worked up (for example, drying and concentration) togive the compound (M-7).

Reference Process 2

The compound (M-5) may be prepared by undergoing a dealkylation to acompound represented by formula (M-8) (hereinafter, referred to asCompound (M-8)) in the presence of an acid.

[wherein, R⁴⁰ represents a methyl group or an ethyl group, and the othersymbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated aliphatichydrocarbons, aromatic hydrocarbons, nitriles, alcohols, acetic acid,water, and mixed solvents thereof.

Examples of the acid to be used in the reaction include inorganic acidssuch as hydrochloric acid; boron halides such as boron trichloride andboron tribromide; and titanium chloride and aluminum chloride.

In the reaction, the acid is usually used within the range of 0.1 to 10molar ratio(s) as opposed to 1 mole of the compound (M-8). When theinorganic acids such as hydrochloric acid are used as an acid in thereaction, the inorganic acids may be used as a solvent.

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvents, and theorganic layers are worked up (for example, drying and concentration) togive the compound (M-5).

Reference Process 3

The compound (M-8) wherein n is 0 (hereinafter, referred to as Compound(M-8a)), the compound (M-8) wherein n is 1 (hereinafter, referred to asCompound (M-8b)), and the compound (M-8) wherein n is 2 (hereinafter,referred to as Compound (M-8c)) may be prepared according to abelow-mentioned method.

[wherein the symbols are the same as defined above.]

First, a process for preparing a compound represented by formula (M-11)(hereinafter, referred to Compound (M-11)) is described.

The compound (M-11) may be prepared by using the compound (M-9) in theplace of the compound (R-2) and using the compound (M-10) in the placeof the compound (M-3) according to the similar method to that describedin Process 3.

The compound (M-10) may be prepared according to the method described inWO 06/097691 or a method described in The Journal Of Organic Chemistry,1995, 60, 7508-7510.

The compound (M-8a) may be prepared by using the compound (M-11) in theplace of the compound (M-1) according to the method described in theprocess 2.

The compound (M-8b) and the compound (M-8c9 may be prepared by using thecompound (M-8a) in the place of the compound (1-n0) according to themethod described in the Process 1.

Reference Process 4

The compound (M-9) may be prepared by reacting a compound represented byformula (M-12) (hereinafter, referred to as Compound (M-12)) with acompound represented by formula (R-7) (hereinafter, referred to asCompound (R-)) in the presence of a base.

[wherein, X¹⁶ represents a fluorine atom, a chlorine atom, or a bromineatom; and the other symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, aprotic polar solvents, and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates, and alkali metal hydrides.

In the reaction, the compound (R-7) is used usually within a range of 1to 10 molar ratio(s), and the base is used usually within a range of 1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-12).

The reaction temperature of the reaction is usually within a range of−20 to 150° C. The reaction period of the reaction is usually within arange of 0.5 to 24 hours.

When the reaction is completed, water is added to the reaction mixtures,and the reaction mixtures are extracted with organic solvent(s), and theorganic layers are worked up (for example, drying and concentration) togive the compound (M-9).

Each of the compound (M-12) and the compound (R-7) is a commerciallyavailable compound, or can be prepared by using a known method.

Reference Process 5

The compound (M-1) may be prepared by reacting a compound represented byformula (M-13) (hereinafter, referred to Compound (M-13)) with thecompound (M-10) in the presence of a metal catalyst.

[wherein, the symbols are the same as defined above.]

The compound (M-1) may be prepared by using the compound (M-13) in theplace of the compound (M-9) according to the method described in theprocess 3 for preparing the compound (M-11).

The compound (M-13) may be prepared by using a known method.

Reference Process 6

The compound (M-14) may be prepared by reacting the compound (M-5) witha compound represented by formula (R-6) (hereinafter, referred to asCompound (R-6)) in the presence of a base.

[wherein, the symbols are the same as defined above.]

The compound (R-6) is a commercially available compound, or can beprepared by using a known method.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, aprotic polar solvents, and mixed solventsthereof.

Examples of the base to be used in the reaction include organic basessuch as diisopropylethylamine and 2,6-lutidine, alkali metal hydrides,and alkali metal carbonates.

In the reaction, the compound (R-6) is usually used within a range of 1to 2 molar ratio(s), and the base is usually used within a range of 1 to10 molar ratio(s), as opposed to 1 mole of the compound (M-5).

The reaction temperature of the reaction is usually within a range of−20 to 150° C. The reaction period of the reaction is usually within arange of 0.5 to 24 hours.

When the reaction is completed, water is added to reaction mixtures, andthe reaction mixtures are extracted with organic solvent(s), and theorganic layers are worked up (for example, drying and concentration) togive the compound (M-14).

Next, specific examples of the compound of the present invention areindicated below.

A compound represented by formula (L-1):

(hereinafter, referred to as Compound (L-1)) wherein Het¹ representsH-1:

and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX1).

TABLE 1 R¹⁰⁰ R¹⁰¹ R¹⁰² R¹⁰³ R¹⁰⁴ H CF₃ H H H H H CF₃ H H H OCF₃ H H H HH OCF₃ H H H SCF₃ H H H H S(O)CF₃ H H H H S(O)₂CF₃ H H H H H SCF₃ H H HH S(O)CF₃ H H H H S(O)₂CF₃ H H H OS(O)₂CF₃ H H H H H OS(O)₂CF₃ H H H CF₃CF₃ H H H CF₃ F H H H CF₃ Cl H H H CF₃ CN H H H CF₃ NO₂ H H H CF₃ COOCH₃H H H CF₃ N(CH₃)₂ H H

TABLE 2 R¹⁰⁰ R¹⁰¹ R¹⁰² R¹⁰³ R¹⁰⁴ H CF₃ H CF₃ H H CF₃ H F H H CF₃ H Cl HH CF₃ H CN H H CF₃ H NO₂ H H CF₃ H COOCH₃ H H CF₃ H N(CH₃)₂ H H CF₃ H HCF₃ H CF₃ H H F H CF₃ H H Cl H CF₃ H H CN H CF₃ H H NO₂ H CF₃ H H COOCH₃H CF₃ H H N(CH₃)₂

TABLE 3 R¹⁰⁰ R¹⁰¹ R¹⁰² R¹⁰³ R¹⁰⁴ H F CF₃ H H H Cl CF₃ H H H CN CF₃ H H HNO₂ CF₃ H H H COOCH₃ CF₃ H H H N(CH₃)₂ CF₃ H H CF₃ H CF₃ H H F H CF₃ H HCl H CF₃ H H CN H CF₃ H H NO₂ H CF₃ H H COOCH₃ H CF₃ H H N(CH₃)₂ H CF₃ HH H F H F H H F F F H H Cl H Cl H H Cl Cl Cl H

The compound (L-1) wherein Het¹ represents H-2:

and R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituents indicated inTable 4 to Table 6 (hereinafter, referred to as Compound Class SX2).

TABLE 4 R¹⁰¹ R¹⁰² R¹⁰³ R¹⁰⁴ CF₃ H H H H CF₃ H H H H CF₃ H OCF₃ H H H HOCF₃ H H H H OCF₃ H SCF₃ H H H S(O)CF₃ H H H S(O)₂CF₃ H H H H SCF₃ H H HS(O)CF₃ H H H S(O)₂CF₃ H H H H SCF₃ H H H S(O)CF₃ H H H S(O)₂CF₃ HOS(O)₂CF₃ H H H H OS(O)₂CF₃ H H H H OS(O)₂CF₃ H

TABLE 5 R¹⁰¹ R¹⁰² R¹⁰³ R¹⁰⁴ CF₃ CF₃ H H CF₃ F H H CF₃ Cl H H CF₃ CN H HCF₃ H CF₃ H CF₃ H F H CF₃ H Cl H CF₃ H CN H H CF₃ CF₃ H H CF₃ F H H CF₃Cl H H CF₃ CN H H F CF₃ H H Cl CF₃ H H CN CF₃ H

TABLE 6 R¹⁰¹ R¹⁰² R¹⁰³ R¹⁰⁴ F CF₃ H H Cl CF₃ H H CN CF₃ H H F H CF₃ H ClH CF₃ H CN H CF₃ H F H F H F F F H Cl H Cl H Cl Cl Cl H

The compound (L-1) wherein Het¹ represents H-3:

and R¹⁰⁰, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituents indicated inTable 7 to Table 8 (hereinafter, referred to as Compound Class SX3).

TABLE 7 R¹⁰⁰ R¹⁰² R¹⁰³ R¹⁰⁴ H CF₃ H H H OCF₃ H H H SCF₃ H H H S(O)CF₃ HH H S(O)₂CF₃ H H H OS(O)₂CF₃ H H H H CF₃ H H H OCF₃ H H H SCF₃ H H HS(O)CF₃ H H H S(O)₂CF₃ H H H OS(O)₂CF₃ H

TABLE 8 R¹⁰⁰ R¹⁰² R¹⁰³ R¹⁰⁴ H Cl CF₃ H H Cl OCF₃ H H Cl SCF₃ H H ClS(O)CF₃ H H Cl S(O)₂CF₃ H H Cl OS(O)₂CF₃ H H CF₃ Cl H H OCF₃ Cl H H SCF₃Cl H H S(O)CF₃ Cl H H S(O)₂CF₃ Cl H H OS(O)₂CF₃ Cl H H F H H H H F H H FF H H Cl H H H H Cl H H Cl Cl H

The compound (L-1) wherein Het¹ represents H-4:

and R¹⁰⁰, R¹⁰¹, R¹⁰³, and R⁰⁴ represents any substituents indicated inTable 9 (hereinafter, referred to as Compound Class SX4).

TABLE 9 R¹⁰⁰ R¹⁰¹ R¹⁰³ R¹⁰⁴ H CF₃ H H H OCF₃ H H H SCF₃ H H H S(O)CF₃ HH H S(O)₂CF₃ H H H OS(O)₂CF₃ H H H CF₃ CF₃ H H CF₃ F H H CF₃ Cl H H F HH H Cl H H H F F H H Cl Cl H

The compound (L-1) wherein Het¹ represents H-5:

and R¹⁰⁰, R¹⁰¹, R¹⁰², and R¹⁰³ represents any substituents indicated inTable 10 to Table 11 (hereinafter, referred to as Compound Class SX5).

TABLE 10 R¹⁰⁰ R¹⁰¹ R¹⁰² R¹⁰³ H CF₃ H H H OCF₃ H H H SCF₃ H H H S(O)CF₃ HH H S(O)₂CF₃ H H H OS(O)₂CF₃ H H H H CF₃ H H H OCF₃ H H H SCF₃ H H HS(O)CF₃ H H H S(O)₂CF₃ H H H OS(O)₂CF₃ H H H H CF₃ H H H OCF₃ H H H SCF₃H H H S(O)CF₃ H H H S(O)₂CF₃ H H H OS(O)₂CF₃

TABLE 11 R¹⁰⁰ R¹⁰¹ R¹⁰² R¹⁰³ H CF₃ CF₃ H H CF₃ H CF₃ H CF₃ F H H CF₃ ClH H CF₃ H F H CF₃ H Cl H H CF₃ CF₃ H H CF₃ F H H CF₃ Cl H F CF₃ H H ClCF₃ H H F H CF₃ H Cl H CF₃ H H F CF₃ H H Cl CF₃

The compound (L-1) wherein Het¹ represents any one of H-6, H-7, H-8, orH-9:

(hereinafter, referred to as Compound Class SX6).

The compound (L-1) wherein Het¹ represents H-10:

and X²¹, X²² and X²³ represents any groups indicated in Table 12(hereinafter, referred to as Compound Class SX7).

TABLE 12 X²¹ X²² X²³ N CH CH CH N CH CH CH N N N CH CH N N N CH N N N N

The compound (L-1) wherein Het¹ represents H-11:

and X²⁰, X²² and X²³ represents any groups indicated in Table 13(hereinafter, referred to as Compound Class SX8).

TABLE 13 X²⁰ X²² X²³ N CH CH CH N CH CH CH N N N CH CH N N N CH N N N N

A compound represented by formula (L-2):

(hereinafter, referred to as Compound (L-2)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX9);

The compound (L-2) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX10);

The compound (L-2) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX11);

The compound (L-2) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX12);

The compound (L-2) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX13);

The compound (L-2) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX14);

The compound (L-2) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX15).

The compound (L-2) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX16).

A compound represented by formula (L-3):

(hereinafter, referred to as Compound (L-3)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX17);

The compound (L-3) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX18);

The compound (L-3) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX19);

The compound (L-3) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX20);

The compound (L-3) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX21);

The compound (L-3) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX22);

The compound (L-3) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX23).

The compound (L-3) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX24).

A compound represented by formula (L-4):

(hereinafter, referred to as Compound (L-4)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX25);

The compound (L-4) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX26);

The compound (L-4) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX27);

The compound (L-4) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX28);

The compound (L-4) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX29);

The compound (L-4) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX30);

The compound (L-4) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX31).

The compound (L-4) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX32).

A compound represented by formula (L-5):

(hereinafter, referred to as Compound (L-5)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX33);

The compound (L-5) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX34);

The compound (L-5) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX35);

The compound (L-5) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX36);

The compound (L-5) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX37);

The compound (L-5) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX38);

The compound (L-5) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX39).

The compound (L-5) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX40).

A compound represented by formula (L-6):

(hereinafter, referred to as Compound (L-6)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX41);

The compound (L-6) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX42);

The compound (L-6) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX43);

The compound (L-6) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX44);

The compound (L-6) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX45);

The compound (L-6) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX46);

The compound (L-6) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX47).

The compound (L-6) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX48).

A compound represented by formula (L-7):

(hereinafter, referred to as Compound (L-7)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX49);

The compound (L-7) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX50);

The compound (L-7) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX51);

The compound (L-7) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX52);

The compound (L-7) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX53);

The compound (L-7) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX54);

The compound (L-7) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX55).

The compound (L-7) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX56).

A compound represented by formula (L-8):

(hereinafter, referred to as Compound (L-8)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX57);

The compound (L-8) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX58);

The compound (L-8) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX59);

The compound (L-8) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX60);

The compound (L-8) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX61);

The compound (L-8) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX62);

The compound (L-8) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX63).

The compound (L-8) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX64).

A compound represented by formula (L-9):

(hereinafter, referred to as Compound (L-9)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX65);

The compound (L-9) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX66);

The compound (L-9) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX67);

The compound (L-9) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX68);

The compound (L-9) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰⁴ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX69);

The compound (L-9) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX70);

The compound (L-9) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX71).

The compound (L-9) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX72).

A compound represented by formula (L-10):

(hereinafter, referred to as Compound (L-10)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX73);

The compound (L-10) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX74);

The compound (L-10) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX75);

The compound (L-10) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX76);

The compound (L-10) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX77);

The compound (L-10) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX78);

The compound (L-10) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX79).

The compound (L-10) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX80).

A compound represented by formula (L-11):

(hereinafter, referred to as Compound (L-11)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX81);

The compound (L-11) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX82);

The compound (L-11) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX83);

The compound (L-11) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX84);

The compound (L-11) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX85);

The compound (L-11) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX86);

The compound (L-11) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX87).

The compound (L-11) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX88).

A compound represented by formula (L-12):

(hereinafter, referred to as Compound (L-12)) wherein Het¹ representsH-1, and R¹⁰⁰, R¹⁰¹, R¹⁰², R¹⁰³, and R¹⁰⁴ represents any substituentsindicated in Table 1 to Table 3 (hereinafter, referred to as CompoundClass SX89);

The compound (L-12) wherein Het¹ represents H-2, R¹⁰¹, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 4 to Table 6(hereinafter, referred to as Compound Class SX90);

The compound (L-12) wherein Het¹ represents H-3, R¹⁰⁰, R¹⁰², R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 7 to Table 8(hereinafter, referred to as Compound Class SX91);

The compound (L-12) wherein Het¹ represents H-4, R¹⁰⁰, R¹⁰¹, R¹⁰³ andR¹⁰⁴ represents any substituents indicated in Table 9 (hereinafter,referred to as Compound Class SX92);

The compound (L-12) wherein Het¹ represents H-5, R¹⁰⁰, R¹⁰¹, R¹⁰² andR¹⁰³ represents any substituents indicated in Table 10 to Table 11(hereinafter, referred to as Compound Class SX93);

The compound (L-12) wherein Het¹ represents any of H-6, H-7, H-8, or H-9(hereinafter, referred to as Compound Class SX94);

The compound (L-12) wherein Het¹ represents H-10, and X²¹, X²² and X²³represents any groups indicated in Table 12 (hereinafter, referred to asCompound Class SX95).

The compound (L-12) wherein Het¹ represents H-11, and X²⁰, X²² and X²³represents any groups indicated in Table 13 (hereinafter, referred to asCompound Class SX96).

Next, specific examples of production intermediate compound aredescribed below.

A compound represented by formula (L-13):

(hereinafter, referred to as Compound (L-13)) wherein A², A³, and A⁴represent CH, and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, and R²⁰⁵ represent anysubstituents indicated in Table 14 to Table 17);

The compound represented by formula (L-13) wherein A² and A⁴ representCH, A³ represents C(CH₃), and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, and R²⁰⁵ representany substituents indicated in Table 14 to Table 17;

The compound represented by formula (L-13) wherein A² and A⁴ representCH, A³ represents C(OCH₃), and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, and R²⁰⁵represent any substituents indicated in Table 14 to Table 17;

The compound represented by formula (L-13) wherein A² and A⁴ representCH, A³ represents C(NO₂), and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, and R²⁰⁵ representany substituents indicated in Table 14 to Table 17;

The compound represented by formula (L-13) wherein A² represents anitrogen atom, A³ and A⁴ represent CH, and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, andR²⁰⁵ represent any substituents indicated in Table 14 to Table 17;

The compound represented by formula (L-13) wherein A² and A⁴ representCH, A³ represents a nitrogen atom, and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, and R²⁰⁵represent any substituents indicated in Table 14 to Table 17;

The compound represented by formula (L-13) wherein A² and A⁴ representCH, A⁴ represents a nitrogen atom, and R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, and R²⁰⁵represent any substituents indicated in Table 14 to Table 17.

TABLE 14 R²⁰¹ R²⁰² R²⁰³ R²⁰⁴ R²⁰⁵ CF₃ CH₃ H H H CF₃ CH₂CH₃ H H H CF₂CF₃CH₃ H H H CF₂CF₃ CH₂CH₃ H H H CF₂CF₂CF₃ CH₃ H H H CF₂CF₂CF₃ CH₂CH₃ H H HCF₂CF₂CF₃ CH₃ H H H CF₂CF₂CF₃ CH₂CH₃ H H H

TABLE 15 R²⁰¹ R²⁰² R²⁰³ R²⁰⁴ R²⁰⁵ CF₃ CH₂CH₃ H H NH₂ CF₃ CH₂CH₃ H HNHCH₃ CF₂CF₃ CH₂CH₃ H H N(CH₃)₂ CF₂CF₃ CH₂CH₃ H H

CF₂CF₂CF₃ CH₂CH₃ H H

CF₂CF₂CF₃ CH₂CH₃ H H

CF₂CF₂CF₃ CH₂CH₃ H H

TABLE 16 R²⁰¹ R²⁰² R²⁰³ R²⁰⁴ R²⁰⁵ CF₃ CH₂CH₃ H

H CF₃ CH₂CH₃ H

H CF₂CF₃ CH₂CH₃ H

H CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H

TABLE 17 R²⁰¹ R²⁰² R²⁰³ R²⁰⁴ R²⁰⁵ CF₂CF₂CF₃ CH₂CH₃ H OCH₃ H CF₂CF₂CF₃CH₂CH₃ H OCH₂CH₃ H CF₂CF₂CF₃ CH₂CH₃ H OCH₂CH₂CH₃ H CF₂CF₂CF₃ CH₂CH₃ HOCH₂CH₂CH₂CH₃ H CF₂CF₂CF₃ CH₂CH₃ H OCH(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₃ HOCH₂CF₃ H CF₂CF₂CF₃ CH₂CH₃ H OCH₂CF₂CF₂H H CF₂CF₂CF₃ CH₂CH₃ H OCH₂CF₂CF₃H CF₂CF₂CF₃ CH₂CH₃ H OCF₃ H CF₂CF₂CF₃ CH₂CH₃ H OCF₂CF₂H H CF₂CF₂CF₃CH₂CH₃ H CF₃ H CF₂CF₂CF₃ CH₂CH₃ H CF₂CF₃ H CF₂CF₂CF₃ CH₂CH₃ H CF₂CF₂H HCF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H CF₂CF₂CF₃ CH₂CH₃ H

H

The Present compound may be mixed or combined with one or moreingredient(s) selected from a group consisting of Group (a), Group (b),Group (c), and Group (d) (hereinafter, referred to as Presentingredient).

The above-mentioned mixing or combining represents a use of the Presentcompound and the Present ingredient at same time, separately or atcertain intervals.

When the Present compound and the present ingredient are used at thesame time, the Present compound and the Present ingredient may becontained in separate formulations respectively or may be contained inthe same one formulation.

One aspect of the present invention is a composition comprising one ormore ingredients selected from Group (a), Group (b), Group (c) and Group(d) (that is, Present ingredient) as well as the Present compound.

Group (a) represents an insecticidal ingredient group, a miticidalingredient group, or a nematicidal ingredient group, which is selectedfrom the group consisting of the following sub group a-1 to sub groupa-10.

Sub group a-1: Carbamate acetylcholinesterase (AChE) inhibitors

Sub group a-2: Organophosphorus acetylcholinesterase (AChE) inhibitors

Sub group a-3: GABA-gated chloride channel blockers

Sub group a-4: GABA-gated chloride channel allosteric modulators

Sub group a-5: Sodium channel modulators

Sub group a-6: Nicotinic acetylcholine receptor (nAChR) competitivemodulators

Sub group a-7: Ryanodine receptor modulators

Sub group a-8: Microbial materials

Sub group a-9: Nematicidal ingredients

Sub group a-10: The other group as insecticidal active ingredients andmiticidal active ingredients

Group (b) represents a fungicidal active ingredient group selected fromthe group consisting of the following sub group b-1 to sub group b-18.

Sub group b-1: PA fungicides (Phenyl amide)

Sub group b-2: MBC fungicides (methyl benzimidazole carbamate)

Sub group b-3: Thiazole carboxamides

Sub group b-4: SDHI (Succinate dehydrogenase inhibitors)

Sub group b-5: QoI fungicides (Qo Inhibitors)

Sub group b-6: QiI fungicides (Qi Inhibitors)

Sub group b-7: Thiophene carboxamides

Sub group b-8: AP fungicides (Anilinopyrimidine)

Sub group b-9: PP fungicides (Phenylpyrrole)

Sub group b-10: AH fungicides (Aromatic hydrocarbons)

Sub group b-11: DMI fungicides (Demethylation inhibitors)

Sub group b-12: CCA fungicides (Carboxylic acid amide)

Sub group b-13: Piperidinyl thiazole isoxazoline

Sub group b-14: Tetrazolyl oxime

Sub group b-15: Dithiocarbamate

Sub group b-16: Phthalimide

Sub group b-17: Microbial fungicides

Sub group b-18: Other fungicides

Group (c) represents a plant growth modulating ingredients groupselected from the group consisting of the following sub group c-1, subgroup c-2, and sub group c-3.

Sub group c-1: Plant growth modulating compounds

Sub group c-2: Mycorrhizal fungi group

Sub group c-3: Root nodule bacteria group

Group (d) represents a phytotoxicity-reducing ingredient group.

The composition comprising the above-mentioned present ingredients andthe present compounds can exert their efficacies of the compositiondepending on the content or the content ratio of the above-mentionedpresent ingredients and the present compounds contained in thecomposition. Accordingly, the usage of the above-mentioned compositionmay be decided depending on the effect that is expressed by theabove-mentioned composition. The above-mentioned composition may haveone or two usages therefor.

One aspect of above-mentioned composition is an agrochemicalcomposition.

Another aspect of the above-mentioned composition is a composition forcontrolling harmful arthropods.

Another aspect of the above-mentioned composition is an insecticidal,miticidal or nematicidal composition.

Another aspect of the above-mentioned composition is a fungicidalcomposition.

Another aspect of the above-mentioned composition is a plant growthmodulating composition.

Another aspect of the above-mentioned composition is aphytotoxicity-reducing composition.

Examples of the combination of the Present ingredient and the Presentcompound are described below. For example, “akanicarb+SX” represents acombination of alanycarb and SX. The symbol of “SX” represents any oneof the Present compound selected from the Compound Class SX1 to theCompound Class SX96. Also, all of the below-mentioned present ingredientare known ingredients, and are commercially available or may be producedby the known method. If the present ingredient is a bacteria, it isavailable from the bacterial authority depository. The numerical numberin bracket represents a CAS register number.

Examples of the combination of the Present ingredient of the above subgroup a-1 and the Present compound:

alanycarb+SX, aldicarb+SX, bendiocarb+SX, benfuracarb+SX,butocarboxim+SX, butoxycarboxim+SX, carbaryl: NAC+SX, carbofuran+SX,carbosulfan+SX, ethiofencarb+SX, fenobucarb: BPMC+SX, formetanate+SX,furathiocarb+SX, isoprocarb: MIPC+SX, methiocarb+SX, methomyl+SX,metolcarb+SX, oxamyl+SX, pirimicarb+SX, propoxur: PHC+SX, thiodicarb+SX,thiofanox+SX, triazamate+SX, trimethacarb+SX, XMC+SX, xylylcarb+SX.

Examples of the combination of the Present ingredient of the above subgroup a-2 and the Present compound:

acephate+SX, azamethiphos+SX, azinphos-ethyl+SX, azinphos-methyl+SX,cadusafos+SX, chlorethoxyfos+SX, chlorfenvinphos+SX, chlormephos+SX,chlorpyrifos+SX, chlorpyrifos-methyl+SX, coumaphos+SX, cyanophos:CYAP+SX, demeton-S-methyl+SX, diazinon+SX, dichlorvos: DDVP+SX,dicrotophos+SX, dimethoate+SX, dimethylvinphos+SX, disulfoton+SX,EPN+SX, ethion+SX, ethoprophos+SX, famphur+SX, fenamiphos+SX,fenitrothion: MEP+SX, fenthion: MPP+SX, fosthiazate+SX, heptenophos+SX,imicyafos+SX, isofenphos+SX,isopropyl-O-(methoxyaminothiophosphoryl)salicylate+SX, isoxathion+SX,malathion+SX, mecarbam+SX, methamidophos+SX, methidathion: DMTP+SX,mevinphos+SX, monocrotophos+SX, naled: BRP+SX, omethoate+SX,oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, phenthoate:PAP+SX, phorate+SX, phosalone+SX, phosmet: PMP+SX, phosphamidon+SX,phoxim+SX, pirimiphos-methyl+SX, profenofos+SX, propetamphos+SX,prothiofos+SX, pyraclofos+SX, pyridaphenthion+SX, quinalphos+SX,sulfotep+SX, tebupirimfos+SX, temephos+SX, terbufos+SX,tetrachlorvinphos+SX, thiometon+SX, triazophos+SX, trichlorfon: DEP+SX,vamidothion+SX.

Examples of the combination of the Present ingredient of the above subgroup a-3 and the Present compound:

ethiprole+SX, fipronil+SX, flufiprole+SX, chlordane+SX, endosulfan+SX,alpha-endosulfan+SX.

Examples of the combination of the Present ingredient of the above subgroup a-4 and the Present compound:

afoxolaner+SX, fluralaner+SX, broflanilide+SX, fluxametamide+SX.

Examples of the combination of the Present active ingredient of theabove sub group a-5 and the Present compound:

acrinathrin+SX, allethrin+SX, bifenthrin+SX, kappa-bifenthrin+SX,bioallethrin+SX, bioresmethrin+SX, cycloprothrin+SX, cyfluthrin+SX,beta-cyfluthrin+SX, cyhalothrin+SX, gamma-cyhalothrin+SX,lambda-cyhalothrin+SX, cypermethrin+SX, alpha-cypermethrin+SX,beta-cypermethrin+SX, theta-cypermethrin+SX, zeta-cypermethrin+SX,cyphenothrin+SX, deltamethrin+SX, empenthrin+SX, esfenvalerate+SX,etofenprox+SX, fenpropathrin+SX, fenvalerate+SX, flucythrinate+SX,flumethrin+SX, fluvalinate+SX, tau-fluvalinate+SX, halfenprox+SX,heptafluthrin+SX, imiprothrin+SX, kadethrin+SX, meperfluthrin+SX,momfluorothrin+SX, permethrin+SX, phenothrin+SX, prallethrin+SX,pyrethrins+SX, resmethrin+SX, silafluofen+SX, tefluthrin+SX,kappa-tefluthrin+SX, tetramethrin+SX, tetramethylfluthrin+SX,tralomethrin+SX, transfluthrin+SX, benfluthrin+SX, flufenoprox+SX,flumethrin+SX, sigma-cypermethrin+SX, furamethrin+SX, metofluthrin+SX,profluthrin+SX, dimefluthrin+SX, epsilon-metofluthrin+SX,epsilon-momfluorothrin+SX, methoxychlor+SX.

Examples of the combination of the Present ingredient of the above subgroup a-6 and the Present compound:

acetamiprid+SX, clothianidin+SX, dinotefuran+SX, imidacloprid+SX,nitenpyram+SX, thiacloprid+SX, thiamethoxam+SX, sulfoxaflor+SX,flupyradifurone+SX, triflumezopyrim+SX, dicloromezotiaz+SX,cycloxaprid+SX,(E)-N-{1-[(6-chloropyridin-3-yl)methyl]pyridine-2(1H)-ylidene}-2,2,2-trifluoroacetamide(1689566-03-7)+SX.

Examples of the combination of the Present active ingredient of theabove sub group a-7 and the Present compound:

chlorantraniliprole+SX, cyantraniliprole+SX, cycloniliprole+SX,flubendiamide+SX, tetraniliprole+SX, cyhalodiamide+SX, a compoundrepresented by the following formula:

(1104384-14-6)+SX.

Examples of the combination of the Present ingredient of the above subgroup a-8 and the Present compound:

Beauveria bassiana+SX, Beauveria brongniartii+SX, Paecilomycesfumosoroseus+SX, Paecilomyces lilacinus+SX, Paecilomyces tenuipes+SX,Verticillium lecani+SX, Arthrobotrys dactyloides+SX, Bacillusthuringiensis+SX, Bacillus firmus+SX, Bacillus megaterium+SX, Hirsutellarhossiliensis+SX, Hirsutella minnesotensis+SX, Monacrosporiumphymatopagus+SX, Pasteuria nishizawae+SX, Pasteuria penetrans+SX,Pasteuria usgae+SX, Verticillium chlamydosporium+SX.

Examples of the combination of the Present ingredient of the above subgroup a-9 and the Present compound:

abamectin+SX, fluazaindolizine+SX, fluensulfone+SX, fluopyram+SX,tioxazafen+SX.

Examples of the combination of the Present ingredient of the above subgroup a-10 and the Present compound:

spinetoram+SX, spinosad+SX, emamectin-benzoate+SX, lepimectin+SX,milbemectin+SX, hydroprene+SX, kinoprene+SX, methoprene+SX,fenoxycarb+SX, pyriproxyfen+SX, methyl bromide+SX, chloropicrin+SX,sulfuryl fluoride+SX, sodium aluminium fluoride or chiolite+SX,borax+SX, boric acid+SX, disodium octaborate+SX, sodium borate+SX,sodium metaborate+SX, tartar emetic+SX, dazomet+SX, metam+SX,pymetrozine+SX, pyrifluquinazone+SX, clofentezine+SX, hexythiazox+SX,diflovidazin+SX, etoxazole+SX, diafenthiuron+SX, azocyclotin+SX,cyhexatin+SX, fenbutatin oxide+SX, propargite+SX, tetradifon+SX,chlorfenapyr+SX, DNOC+SX, sulfluramid+SX, bensultap+SX, cartap+SX,cartap hydrochloride+SX, thiocyclam+SX, thiosultap-disodium+SX,thiosultap-monosodium+SX, bistrifluron+SX, chlorfluazuron+SX,diflubenzuron+SX, fluazuron+SX, flucycloxuron+SX, flufenoxuron+SX,hexaflumuron+SX, lufenuron+SX, novaluron+SX, noviflumuron+SX,teflubenzuron+SX, triflumuron+SX, buprofezin+SX, cyromazine+SX,chromafenozide+SX, halofenozide+SX, methoxyfenozide+SX, tebufenozide+SX,amitraz+SX, hydramethylnon+SX, acequinocyl+SX, fluacrypyrim+SX,bifenazate+SX, fenazaquin+SX, fenpyroximate+SX, pyridaben+SX,pyrimidifen+SX, tebufenpyrad+SX, tolfenpyrad+SX, rotenone+SX,indoxacarb+SX, metaflumizone+SX, spirodiclofen+SX, spiromesifen+SX,spirotetramat+SX, aluminium phosphide+SX, calcium phosphide+SX,phosphine+SX, zinc phosphide+SX, calcium cyanide+SX, potassiumcyanide+SX, sodium cyanide+SX, cyenopyrafen+SX, cyflumetofen+SX,pyflubumide+SX, flonicamid+SX, azadirachtin+SX, benzoximate+SX,bromopropylate+SX, chinomethionat+SX, dicofol+SX, pyridalyl+SX, limesulfur+SX, sulfur+SX, machine oil+SX, nicotine+SX, nicotine-sulfate+SX,afidopyropen+SX, flometoquin+SX, metoxadiazone+SX, pyriminostrobin+SX,

-   N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide    (1477919-27-9)+SX,-   N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide    (1477919-27-9)+SX,-   5-(1,3-dioxan-2-yl)-4-[4-(trifluoromethyl)benzyloxy]pyridine    (1449021-97-9)+SX.

Examples of the combination of the Present active ingredient of theabove sub group b-1 and the Present compound:

benalaxyl+SX, benalaxyl-M+SX, furalaxyl+SX, metalaxyl+SX,metalaxyl-M+SX, oxadixyl+SX, ofurace+SX.

Examples of the combination of the Present ingredient of the above subgroup b-2 and the Present compound:

benomyl+SX, carbendazim+SX, fuberidazole+SX, thiabendazole+SX,thiophanate+SX, thiophanate-methyl+SX.

Examples of the combination of the Present ingredient of the above subgroup b-3 and the Present compound:

ethaboxam+SX.

Examples of the combination of the Present ingredient of the above subgroup b-4 and the Present compound:

benodanil+SX, flutolanil+SX, mepronil+SX, isofetamid+SX, fenfuram+SX,carboxin+SX, oxycarboxin+SX, thifluzamide+SX, benzovindiflupyr+SX,bixafen+SX, fluxapyroxad+SX, furametpyr+SX, isopyrazam+SX, penflufen+SX,penthiopyrad+SX, sedaxane+SX, pydiflumetofen+SX, boscalid+SX,pyraziflumid+SX,

-   3-difluoromethyl-N-methoxy-1-methyl-N-[(1R)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazol-4-carboxamide    (1639015-48-7)+SX,-   3-difluoromethyl-N-methoxy-1-methyl-N-[(1S)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazol-4-carboxamide    (1639015-49-8)+SX,-   N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-chloro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide    (1255734-28-1)+SX,-   3-difluoromethyl-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide    (141573-94-6)+SX,-   3-difluoromethyl-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide    (1352994-67-2)+SX,-   3-difluoromethyl-N-(7-fluoro-1,1,3-trimethylindan-4-yl)-1-methylpyrazole-4-carboxamide    (1383809-87-7)+SX,-   3-difluoromethyl-N-[(3R)-7-fluoro-1,1,3-trimethylindan-4-yl]-1-methylpyrazole-4-carboxamide    (1513466-73-3)+SX.

Examples of the combination of the Present ingredient of the above subgroup b-5 and the Present compound:

azoxystrobin+SX, coumoxystrobin+SX, enoxastrobin+SX,flufenoxystrobin+SX, picoxystrobin+SX, pyraoxystrobin+SX,mandestrobin+SX, pyraclostrobin+SX, pyrametostrobin+SX,triclopyricarb+SX, kresoxim-methyl+SX, trifloxystrobin+SX,dimoxystrobin+SX, fenaminstrobin+SX, metominostrobin+SX,orysastrobin+SX, famoxadone+SX, fluoxastrobin+SX, fenamidone+SX,pyribencarb+SX.

Examples of the combination of the Present ingredient of the above subgroup b-6 and the Present compound:

cyazofamid+SX, amisulbrom+SX, binapacryl+SX, meptyldinocap+SX,dinocap+SX, fluazinam+SX.

Examples of the combination of the Present ingredient of the above subgroup b-7 and the Present compound:

silthiofam+SX.

Examples of the combination of the Present active ingredient of theabove sub group b-8 and the Present compound:

cyprodinil+SX, mepanipyrim+SX, pyrimethanil+SX.

Examples of the combination of the Present ingredient of the above subgroup b-9 and the Present compound:

fenpiclonil+SX, fludioxonil+SX.

Examples of the combination of the Present ingredient of the above subgroup b-10 and the Present compound:

biphenyl+SX, chloroneb+SX, dicloran+SX, quintozene+SX, tecnazene+SX,tolclofos-methyl+SX.

Examples of the combination of the Present ingredient of the above subgroup b-11 and the Present compound:

azaconazole+SX, bitertanol+SX, bromuconazole+SX, cyproconazole+SX,difenoconazole+SX, diniconazole+SX, diniconazole-M+SX, epoxiconazole+SX,etaconazole+SX, fenbuconazole+SX, fluquinconazole+SX, flusilazole+SX,flutriafol+SX, hexaconazole+SX, imibenconazole+SX, ipconazole+SX,ipfentrifluconazole+SX, mefentrifluconazole+SX, metconazole+SX,myclobutanil+SX, penconazole+SX, propiconazole+SX, simeconazole+SX,tebuconazole+SX, tetraconazole+SX, triadimefon+SX, triadimenol+SX,triticonazole+SX, prothioconazole+SX, triforine+SX, pyrifenox+SX,pyrisoxazole+SX, fenarimol+SX, nuarimol+SX, imazalil+SX,oxpoconazole+SX, oxpoconazole fumarate+SX, pefurazoate+SX,prochloraz+SX, triflumizole+SX.

Examples of the combination of the Present ingredient of the above subgroup b-12 and the Present compound:

dimethomorph+SX, flumorph+SX, pyrimorph+SX, benthiavalicarb+SX,benthivalicarb-isopropyl+SX, iprovalicarb+SX, valifenalate+SX,mandipropamid+SX.

Examples of the combination of the Present ingredient of the above subgroup b-13 and the Present compound:

oxathiapiprolin+SX.

Examples of the combination of the Present ingredient of the above subgroup b-14 and the Present compound:

picarbutrazox+SX.

Examples of the combination of the Present ingredient of the above subgroup b-15 and the Present compound:

ferbam+SX, mancozeb+SX, maneb+SX, metiram+SX, propineb+SX, thiram+SX,zineb+SX, ziram+SX.

Examples of the combination of the Present active ingredient of theabove sub group b-16 and the Present compound:

captan+SX, captafol+SX, folpet+SX.

Examples of the combination of the Present ingredient of the above subgroup b-17 and the Present compound:

Agrobacterium radiobactor strains (such as its 84 strain)+SX, Bacillusamyloliquefaciens+SX, Bacillus amyloliquefaciens strain QST713+SX,Bacillus amyloliquefaciens strain FZB24+SX, Bacillus amyloliquefaciensstrain MBI600+SX, Bacillus amyloliquefaciens strain D747+SX, Bacillusamyloliquefaciens strain AT332+SX, Bacillus amyloliquefaciens strainPTA4838+SX, Bacillus pumilus+SX, Bacillus simplex CGF2856 strains (suchas its CGF2856 strain)+SX, Bacillus subtilis+SX, Bacillus subtilisstrain QST713+SX, Bacillus subtilis strain HAI0404+SX, Bacillus subtilisstrain Y1336+SX, Variovorax paradoxus strains (such as its CGF4526strain)+SX, Erwinia carotovora strains (such as its CGE234M403strain)+SX, Pseudomonas fluorescens strains (such as its G7090strain)+SX, Talaromyces flavus strains (such as its SAY-Y-94-01strain)+SX, Trichoderma atroviride strains (such as its SKT-1strain)+SX, Trichoderma harzianum strains+SX, Harpin protein+SX.

Examples of the combination of the Present ingredient of the above subgroup b-18 and the Present compound:

bupirimate+SX, dimethirimol+SX, ethirimol+SX, hymexazole+SX,octhilinone+SX, oxolinic acid+SX, diethofencarb+SX, zoxamide+SX,pencycuron+SX, fluopicolide+SX, phenamacril+SX, diflumetorim+SX,tolfenpyrad+SX, fentin acetate+SX, fentin chloride+SX, fentinhydroxide+SX, ametoctradin+SX, blasticidin-S+SX, kasugamycin+SX,streptomycin+SX, oxytetracycline+SX, quinoxyfen+SX, proquinazid+SX,chlozolinate+SX, dimethachlone+SX, iprodione+SX, procymidone+SX,vinclozolin+SX, edifenphos+SX, iprobenfos+SX, pyrazophos+SX,isoprothiolane+SX, etridiazole+SX, iodocarb+SX, propamocarb+SX,prothiocarb+SX, aldimorph+SX, dodemorph+SX, fenpropidin+SX,fenpropimorph+SX, piperalin+SX, spiroxamine+SX, tridemorph+SX,fenhexamid+SX, fenpyrazamine+SX, pyributicarb+SX, naftifine+SX,terbinafine+SX, polyoxins+SX, phthalide+SX, pyroquilon+SX,tricyclazole+SX, carpropamid+SX, diclocymet+SX, fenoxanil+SX,tolprocarb+SX, acibenzolar-S-methyl+SX, probenazole+SX, tiadinil+SX,isotianil+SX, laminarin+SX, cymoxanil+SX, fosetyl+SX, teclofthalam+SX,triazoxide+SX, flusulfamide+SX, diclomezine+SX, methasulfocarb+SX,cyflufenamid+SX, metrafenone+SX, pyriofenone+SX, dodine+SX,flutianil+SX, ferimzone+SX, tebufloquin+SX, validamycin+SX, basic copperchloride+SX, copper(II) hydroxide+SX, basic copper sulphate+SX,Dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt(DBEDC)+SX, organocopper+SX, sulfur+SX, chlorothalonil+SX,dichlofluanid+SX, tolylfluanid+SX, guazatine+SX, iminoctadine+SX,anilazine+SX, dithianon+SX, chinomethionat+SX, fluoroimide+SX,dipymetitrone+SX, quinofumelin+SX, dichlobentiazox+SX,

-   3-chloro-5-phenyl-6-methyl-4-(2,6-difluorophenyl)pyridazine    (1358061-55-8)+SX,    fenpicoxamid+SX,-   N′-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy-2,5-dimethylphenyl]-N-ethyl-N-methylmethaneimidamide    (1202781-91-6)+SX,-   2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl=methanesulfonate    (1360819-11-9)+SX,-   4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine    (1362477-26-6)+SX,-   2,2-dimethyl-9-fluoro-5-(quinolin-3-yl)-2,3-dihydrobenzo[f][1,4]oxazepine    (1207749-50-5)+SX,-   2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline    (1257056-97-5)+SX,-   5-fluoro-2-[(4-methylphenyl)methoxy]-4-pyrimidineamine    (1174376-25-0)+SX,-   5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2(1H)-one    (1616664-98-2)+SX,-   N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethaneimidamide    (1052688-31-9)+SX,-   N′-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethaneimidamide    (929908-57-6)+SX,-   ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6)+SX,-   N-{(2-chlorothiazol-5-yl)methyl}-N-ethyl-6-methoxy-3-nitropyridine-2-amine    (1446247-98-8)+SX,-   1-[2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)-3-methylphenyl]-4-methyl-5-oxo-4,5-dihydro-1H-tetrazole    (1472649-01-6)+SX.

Examples of the combination of the Present ingredient of the above subgroup c-1 and the Present compound:

ethephon+SX, chlormequat+SX, chlormequat-chloride+SX, mepiquat+SX,mepiquat-chloride+SX, Gibberellin A3+SX, abscisic acid+SX, Kinetin+SX,benzyladenine+SX, forchlorfenuron+SX, thidiazuron+SX.

Examples of the combination of the Present ingredient of the above subgroup c-2 and the Present compound:

Glomus spp.+SX, Glomus intraradices+SX, Glomus mosseae+SX, Glomusaggregatum+SX, Glomus etunicatum+SX.

Examples of the combination of the Present ingredient of the above subgroup c-3 and the Present compound:

Bradyrhizobium elkani+SX, Bradyrhizobium japonicum+SX, Bradyrhizobiumlupini+SX, Rhizobium leguminosarum bv. trifolii+SX, Rhizobiumleguminosarum bv. phaseoli+SX, Rhizobium leguminosarum bv. viciae+SX,Sinorhizobium meliloti+SX, Rhizobium spp.+SX.

Examples of the combination of the Present active ingredient of theabove sub group d and the Present compound:

benoxacor+SX, cloquintocet-mexyl+SX, cyometrinil+SX, dichlormid+SX,fenchlorazole-ethyl+SX, fenclorim+SX, flurazole+SX, furilazole+SX,mefenpyr-diethyl+SX, MG191(2-(dichloromethyl)-2-methyl-1,3-dioxolane)+SX, oxabetrinil+SX,allidochlor+SX, isoxadifen-ethyl+SX, cyprosulfamide+SX, fluxofenim+SX,1,8-naphthalic anhydride+SX, AD-674-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane)+SX.

Examples of the harmful arthropod on which the compound of the presentinvention has efficacies include harmful insects and harmful mites.Specific examples of harmful arthropods include the followings.

Hemiptera Pests:

Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens,Sogatella furcifera, Peregrinus maidis, Javesella pellucida,Perkinsiella saccharicida, or Tagosodes orizicolus);

Cicadellidae (for example, Nephotettix cincticeps, Nephotettixvirescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii,Empoasca fabae, Dalbulus maidis, or Cofana spectra);

Cercopidae (for example, Mahanarva posticata, or Mahanarva fimbriolata);

Aphididae (for example, Aphis fabae, Aphis glycines, Aphis gossypii,Aphis pomi, Aphis spiraecola, Myzus persicae, Brachycaudus helichrysi,Brevicoryne brassicae, Rosy apple aphid (Dysaphis plantaginea), Lipaphiserysimi, Macrosiphum euphorbiae, Aulacorthum solani, Nasonoviaribisnigri, Rhopalosiphum padi, Rhopalosiphum maidis, Toxopteracitricidus, Hyalopterus pruni, Melanaphis sacchari, Tetraneuranigriabdominalis, Ceratovacuna lanigera, or Eriosoma lanigerum);

Phylloxeridae (for example, Daktulosphaira vitifoliae, Pecan phylloxera(Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis),or Southern pecan leaf phylloxera (Phylloxera russellae));

Adelgidae (for example, Adelges tsugae, Adelges piceae, or Aphrastasiapectinatae);

Pentatomidae (for example, Scotinophara lurida, Malayan rice black bug(Scotinophara coarctata), Nezara antennata, Eysarcoris aeneus,Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita,Halyomorpha halys, Nezara viridula, Brown stink bug (Euschistus heros),Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelopsmelacanthus);

Cydnidae (for example, Burrower brown bug (Scaptocoris castanea));

Alydidae (for example, Riptortus pedestris, Leptocorisa chinensis, orLeptocorisa acuta);

Coreidae (for example, Cletus punctiger, or Leptoglossus australis);

Lygaeidae (for example, Caverelius saccharivorus, Togo hemipterus, orBlissus leucopterus);

Miridae (for example, Trigonotylus caelestialium, Stenotusrubrovittatus, Stenodema calcarata, or Lygus lineolaris);

Aleyrodidae (for example, Trialeurodes vaporariorum, Bemisia tabaci,Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, orPealius euryae);

Diaspididae (for example, Abgrallaspis cyanophylli, Aonidiella aurantii,Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis,or Unaspis citri);

Coccidae (for example, Ceroplastes rubens);

Margarodidae (for example, Icerya purchasi, or Icerya seychellarum);

Pseudococcidae (for example, Phenacoccus solani, Phenacoccus solenopsis,Planococcus kraunhiae, Planococcus comstocki, Planococcus citri,Pseudococcus calceolariae, Pseudococcus longispinus, or Brevennia rehi);

Psyllidae (for example, Diaphorina citri, Trioza erytreae, Cacopsyllapyrisuga, Cacopsylla chinensis, Bactericera cockerelli, or Pear psylla(Cacopsylla pyricola));

Tingidae (for example, Corythucha ciliata, Corythucha marmorata,Stephanitis nashi, or Stephanitis pyrioides);

Cimicidae (for example, Cimex lectularius); and

Cicadidae (for example, Giant Cicada (Quesada gigas)).

Lepidoptera

Crambidae (for example, Chilo suppressalis, Darkheaded stem borer (Chilopolychrysus), White stem borer (Scirpophaga innotata), Scirpophagaincertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis,Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, European cornborer (Ostrinia nubilalis), Hellula undalis, Herpetogramma luctuosale,Pediasia teterrellus, Nymphula depunctalis, Sugarcane borer (Diatraeasaccharalis));

Pyralidae (for example, Elasmopalpus lignosellus or Plodiainterpunctella);

Noctuidae (for example, Spodoptera litura, Spodoptera exigua, Mythimnaseparata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia,Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Agrotisipsilon, Autographa nigrisigna, Plusia festucae, Soybean looper(Chrysodeixis includens), Trichoplusia spp., Heliothis spp. (forexample, Heliothis virescens), Helicoverpa armigera, Helicoverpa spp.(for example, Helicoverpa zea), Velvetbean caterpillar (Anticarsiagemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer(Hydraecia immanis)),

Pieridae (for example, Pieris rapae);

Tortricidae (for example, Grapholita molesta, Grapholita dimorpha,Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes oranafasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus,Cydia pomonella, Tetramoera schistaceana, Bean Shoot Borer (Epinotiaaporema), or Citrus fruit borer (Ecdytolopha aurantiana));

Gracillariidae (for example, Caloptilia theivora, or Phyllonorycterringoniella);

Carposinidae (for example, Carposina sasakii);

Lyonetiidae (for example, Coffee Leaf miner (Leucoptera coffeela),Lyonetia clerkella, or Lyonetia prunifoliella);

Lymantriidae (for example, Lymantria spp. (for example, Lymantriadispar), or Euproctis spp. (for example, Euproctis pseudoconspersa));

Pluteliidae (for example, Plutella xylostella);

Gelechiidae (for example, Anarsia lineatella, Helcystogrammatriannulellum, Pectinophora gossypiella, Phthorimaea operculella, orTuta absolut);

Arctiidae (for example, Hyphantria cunea);

Castniidae (for example, Giant Sugarcane borer (Telchin licus));

Cossidae (for example, Cosus insularis);

Geometridae (for example, Ascotis selenaria);

Limacodidae (for example, Parasa lepida);

Stathmopodidae (for example, Stathmopoda masinissa);

Sphingidae (for example, Acherontia lachesis);

Sesiidae (for example, Nokona feralis);

Hesperiidae (for example, Parnara guttata).

Thysanoptera

Thripidae (for example, Frankliniella occidentalis, Thrips palmi,Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa,Stenchaetothrips biformis, or Echinothrips americanus);

Phlaeothripidae (for example, Haplothrips aculeatus).

Diptera

Anthomyiidae (for example, Delia platura or Delia antiqua);

Ulidiidae (for example, Tetanops myopaeformis);

Agromyzidae (for example, Agromyza oryzae, Liriomyza sativae, Liriomyzatrifolii, or Chromatomyia horticola);

Chloropidae (for example, Chlorops oryzae);

Tephritidae (for example, Bactrocera cucurbitae, Bactrocera dorsalis,Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, or Ceratitiscapitata);

Ephydridae (for example, Hydrellia griseola, Hydrellia philippina,Hydrellia sasakii, or Ephydridae);

Drosophilidae (for example, Drosophila suzukii);

Phoridae (for example, Megaselia spiracularis);

Psychodidae (for example, Clogmia albipunctata);

Sciaridae (for example, Bradysia difformis);

Cecidomyiidae (for example, Mayetiola destructor, or Orseolia oryzae);

Diopsidae (for example, Diopsis macrophthalma);

Tipulidae (for example, Tipula aino, Common cranefly (Tipula oleracea),or European cranefly (Tipula paludosa)).

Coleoptera

Chrysomelidae (for example, Diabrotica virgifera virgifera, Diabroticaundecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae,Diabrotica balteata, Cucurbit Beetle (Diabrotica speciosa), Cerotomatrifurcata, Oulema melanopus, Aulacophora femoralis, Phyllotretastriolata, Cabbage flea beetle (Phyllotreta cruciferae), Western blackflea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodeschrysocephala), Leptinotarsa decemlineata, Oulema oryzae, Colaspisbrunnea, Chaetocnema pulicaria, Chaetocnema confi, Epitrix cucumeris,Dicladispa armigera, Grape Colaspis (Colaspis brunnea), southern cornleaf beetle (Myochrous denticollis), Laccoptera quadrimacu, or Epitrixhirtipennis);

Carabidae (for example, Seedcorn beetle (Stenolophus lecontei), orSlender seedcorn beetle (Clivina impressifrons));

Scarabaeidae (for example, Anomala cuprea, Anomala rufocuprea, Anomalaalbopilosa, Popillia japonica, Heptophylla picea, European Chafer(Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., orPhyllophaga spp. (for example, Phyllophaga crinita), Diloboderus spp.(for example, Diloboderus abderus));

Curculionidae (for example, Araecerus coffeae, Cylas formicarius,Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Echinocnemussquameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineatocollis,Anthonomus grandis, Sphenophorus venatus, Southern Corn Billbug(Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus),Sugarcane wiivil (Sphenophorus levis), Scepticus griseus, Scepticusuniformis, Zabrotes subfasciatus, Tomicus piniperda, Coffee Berry Borer(Hypothenemus hampei), Aracanthus spp. (for example, Aracanthus mourei),and cotton root borer (Eutinobothrus brasiliensis));

Tenebrionidae (for example, Tribolium castaneum, or Tribolium confusum);

Coccinellidae (for example, Epilachna vigintioctopunctata);

Bostrychidae (for example, Lyctus brunneus);

Ptinidae;

Cerambycidae (for example, Anoplophora malasiaca, or Migdolus fryanus);

Elateridae (for example, Melanotus okinawensis, Agriotes fuscicollis,Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp.,Limonius spp., or Aeolus spp.); and

Staphylinidae (for example, Paederus fuscipes).

Orthoptera

Acrididae (for example, Locusta migratoria, Dociostaurus maroccanus,Chortoicetes terminifera, Nomadacris septemfasciata, Brown Locust(Locustana pardalina), Tree Locust (Anacridium melanorhodon), ItalianLocust (Calliptamus italicus), Differential grasshopper (Melanoplusdifferentialis), Two striped grasshopper (Melanoplus bivittatus),Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper(Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucida),Schistocerca gregaria, Yellow-winged locust (Gastrimargus musicus),Spur-throated locust (Austracris guttulosa), Oxya yezoensis, Oxyajaponica, or Patanga succincta);

Gryllotalpidae (for example, Gryllotalpa africana);

Gryllidae (for example, Acheta domesticus, or Teleogryllus emma);

Tettigoniidae (for example, Mormon cricket (Anabrus simplex).

Hymenoptera

Tenthredinidae (for example, Athalia rosae, and Athalia japonica); and

Formicidae (for example, Brown leaf-cutting ant (Atta capiguara)).

Blattodea

Blattellidae (for example, Blattella germanica);

Blattidae (for example, Periplaneta fuliginosa, Periplaneta americana,Periplaneta brunnea, or Blatta orientalis);

Termitidae (for example, Reticulitermes speratus, Coptotermesformosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermesformosanus, Neotermes koshunensis, Glyptotermes satsumensis,Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti,Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermesmiyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis,Pericapritermes nitobei, Sinocapritermes mushae, or Cornitermescumulans).

Acari

Tetranychidae (for example, Tetranychus urticae, Tetranychus kanzawai,Tetranychus evansi, Panonychus citri, Panonychus ulmi, or Oligonychusspp.);

Eriophyidae (for example, Aculops pelekassi, Phyllocoptruta citri,Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans,Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri, Aceriatosichella, or Shevtchenkella sp.);

Tarsonemidae (for example, Polyphagotarsonemus latus);

Tenuipalpidae (for example, Brevipalpus phoenicis);

Tuckerellidae;

Ixodidae (for example, Haemaphysalis longicornis, Haemaphysalis flava,Dermacentor taiwanensis, Dermacentor variabilis, Ixodes ovatus, Ixodespersulcatus, Ixodes scapularis, Amblyomma americanum, Boophilusmicroplus, or Rhipicephalus sanguineus);

Acaridae (for example, Tyrophagus putrescentiae, or Tyrophagus similis);

Pyroglyphidae (for example, Dermatophagoides farinae, orDermatophagoides pteronyssinus);

Cheyletidae (for example, Cheyletus eruditus, Cheyletus malaccensis,Cheyletus moorei, or Cheyletiella yasguri);

Sarcoptidae (for example, Otodectes cynotis, or Sarcoptes scabiei);

Demodicidae (for example, Demodex canis);

Listrophoridae;

Haplochthoniidae;

Macronyssidae (for example, Ornithonyssus bacoti, or Ornithonyssussylviarum);

Dermanyssidae (for example, Dermanyssus gallinae);

Trombiculidae (for example, Leptotrombidium akamushi).

The compound (M-14) has an efficacy for controlling harmful arthropod.

The agent for controlling harmful arthropods of the present inventioncomprises the compound of the present invention and an inert activecarrier. The agent for controlling harmful arthropods is usuallyprepared by mixing the compound of the present invention with an inertactive carrier such as solid carrier, liquid carrier or gaseous carrier,and if necessary, adding surfactants and the other auxiliary agents forformulation, to formulate into emulsifiable concentrates, oil solutions,dust formulations, granules, wettable powders, flowables, microcapsules,aerosols, smoking agents, poison baits, resin formulations, shampooformulations, paste-like formulations, foams, carbon dioxideformulations and tablets and the others. Such formulations may beprocessed into mosquito repellent coils, electric mosquito repellentmats, liquid mosquito formulations, smoking agents, fumigants, sheetformulations, spot-on formulations or formulations for oral treatment.Also, the agent for controlling harmful arthropods of the presentinvention may be mixed with other pesticides, miticides, nematicides,fungicides, plant growth regulators, herbicides, and synergists.

The agent for controlling harmful arthropods of the present inventioncomprises usually 0.01 to 95% by weight of the compound of the presentinvention.

Examples of the solid carrier to be used in the formulation include finepowders or granules of clays (for example, kaolin clay, diatomaceousearth, bentonite, Fubasami clay, or acid white clay), synthetic hydratedsilicon oxides, talcs, ceramics, other inorganic minerals (for example,sericite, quartz, sulfur, active carbon, calcium carbonate or hydratedsilica) or chemical fertilizers (for example, ammonium sulfate, ammoniumphosphate, ammonium nitrate, urea or ammonium chloride) and the others;as well as synthetic resins (for Example, polyester resins such aspolypropylene, polyacrylonitrile, polymethylmethacrylate andpolyethylene terephthalate; nylon resins (for Example, nylon-6, nylon-11and nylon-66); polyamide resins; polyvinyl chloride, polyvinylidenechloride, vinyl chloride-propylene copolymers, and the others).

Examples of the above-mentioned liquid carriers include water; alcohols(for example, methanol, ethanol, isopropyl alcohol, butanol, hexanol,benzyl alcohol, ethylene glycol, propylene glycol or phenoxy ethanol);ketones (for Example, acetone, methyl ethyl ketone or cyclohexanone);aromatic hydrocarbons (for example, toluene, xylene, ethyl benzene,dodecyl benzene, phenyl xylyl ethane or methylnaphthalene); aliphatichydrocarbons (for example, hexane, cyclohexane, kerosene or light oil);esters (for example, ethyl acetate, butyl acetate, isopropyl myristate,ethyl oleate, diisopropyl adipate, diisobutyl adipate or propyleneglycol monomethyl ether acetate); nitriles (for Example, acetonitrile orisobutyronitrile); ethers (for example, diisopropyl ether, 1,4-dioxane,ethyleneglycol dimethyl ether, diethyleneglycol dimethyl ether,diethylene glycol monomethyl ether, propylene glycol monomethyl ether,dipropylene glycol monomethyl ether or 3-methoxy-3-methyl-1-butanol);acid amides (for example, dimethylformamide (DMF) or dimethylacetamide);halogenated hydrocarbons (for example, dichloromethane, trichloroethane,carbon tetrachloride); sulfoxides (for example, dimethyl sulfoxide(DMSO)); propylene carbonate; and vegetable oils (for example, soybeanoil or cottonseed oil).

Examples of the above-mentioned gaseous carrier include fluorocarbon,butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbondioxide gas.

Examples of the surfactants include nonionic surfactants such aspolyoxyethylenated alkyl ethers, polyoxyethylenated alkyl aryl ethersand polyethylene glycol fatty acid esters; and anionic surfactants suchas alkyl sulfonates, alkylbenzene sulfonates and alkyl sulfates.

Examples of the other auxiliary agents for formulation include a binder,a dispersant, a colorant and a stabilizer. Specific examples includecasein, gelatin, polysaccharides (for example, starch, gum arabic,cellulose derivatives and alginic acid), lignin derivatives, bentonite,water-soluble synthetic polymers (for example, polyvinyl alcohol,polyvinyl pyrrolidone and polyacrylic acids), PAP (acidic isopropylphosphate), BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixtureof 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of base material of the resin formulation include polyvinylchloride polymers, polyurethane and the others, and a plasticizer suchas phthalate esters (for example, dimethyl phthalate, dioctylphthalate), adipic acid esters and stearic acid may be added to thesebase materials, if necessary. The resin formulation can be prepared bymixing the compound of the present invention with the above-mentionedbase material, kneading the mixture, followed by molding it by injectionmolding, extrusion molding or pressure molding and the like. Theresultant resin formulation can be subjected to further molding orcutting procedure and the like, if necessary, to be processed intoshapes such as a plate, film, tape, net or string shape. These resinformulations can be processed into animal collars, animal ear tags,sheet products, trap strings, gardening supports and other products.

Examples of a base material for the poison baits include baitingredients such as grain powder, vegetable oil, saccharide andcrystalline cellulose, and if necessary, with addition of antioxidantssuch as dibutylhydroxytoluene and nordihydroguaiaretic acid,preservatives such as dehydroacetic acid, accidental ingestioninhibitors for children and pets such as a chili powder, insectattraction fragrances such as cheese flavor, onion flavor and peanutoil.

The method for controlling harmful arthropods of the present inventionis conducted by applying an effective amount of the compound of thepresent invention to a harmful arthropod directly and/or a habitatthereof (for example, plant bodies, soil, an interior of a house, animalbodies). In the method for controlling harmful arthropods of the presentinvention, the Present compound is usually used in the form of an agentfor controlling harmful arthropods.

When an agent for controlling harmful arthropods of the presentinvention is used for controlling harmful arthropods in an agriculturalfield, the application dose as an amount of the compound of the presentinvention is usually within a range from 1 to 10,000 g per 10,000 m².The emulsifiable concentrate, the wettable powder, or the flowableformulation etc. of an agent for controlling harmful arthropods of thepresent invention is usually applied by diluting it with water in such away that a concentration of the compound of the present invention iswithin a range from 0.01 to 10,000 ppm. The granular formulation, or thedust formulation etc., is usually applied as itself without diluting it.

These formulations or an aqueous dilution thereof can be spargeddirectly to harmful arthropods or plants (such as crops) to be protectedfrom harmful arthropods, and also may be applied to the soil of cropland in order to control harmful arthropods which live there.

The resin preparation which is processed into a sheet or a string may beapplied by winding a plant with a sheet or a string of the resinpreparation, putting a string of the resin preparation around a crop sothat the plant is surrounded by the string, or laying a sheet of theresin preparation on the soil surface near the root of a plant.

When the agent for controlling harmful arthropods of the presentinvention is used to control harmful arthropods that live inside ahouse, the application dose as an amount of the Present compound isusually within a range from 0.01 to 1,000 mg per 1 m² of an area to betreated, in the case of using it on a planar area. In the case of usingit spatially, the application dose as an amount of the Present compoundis usually within a range from 0.01 to 500 mg per 1 m³ of the space tobe treated. When the agent for controlling harmful arthropods of thepresent invention is formulated into emulsifiable concentrates, wettablepowders, flowables or the others, such formulations are usually appliedafter diluting it with water in such a way that a concentration of theactive ingredient is within a range from 0.1 to 10,000 ppm, and thensparging it. In the case of being formulated into oil solutions,aerosols, smoking agents, poison baits and the others, such formulationsare used as itself without diluting it.

When the agent for controlling harmful arthropods of the presentinvention is sued for controlling external parasites of livestock suchas cows, horses, pigs, sheep, goats and chickens and small animals suchas dogs, cats, rats and mice, the pest control agent of the presentinvention can be applied to the animals by a known method in theveterinary field. Specifically, when systemic control is intended, thepest control agent of the present invention is administered to theanimals as a tablet, a mixture with feed or a suppository, or byinjection (including intramuscular, subcutaneous, intravenous andintraperitoneal injections). On the other hand, when non-systemiccontrol is intended, the pest control agent of the present invention isapplied to the animals by means of spraying of the oil solution oraqueous solution, pour-on or spot-on treatment, or washing of the animalwith a shampoo formulation, or by putting a collar or ear tag made ofthe resin formulations to the animal. In the case of administering to ananimal body, the dose of the Present compound is usually within a rangefrom 0.1 to 1,000 mg per 1 kg of an animal body weight.

EXAMPLES

Hereinafter, the present invention is explained in more detail by usingPreparation example, Formulation example, and Test example, however, thepresent invention should not be limited to these examples.

First, the preparation example of a compound of the present invention isshown below.

Preparation Example 1

To a mixture of 3-chloropyridine-2-carbonitrile 54 g and THF 300 mL wasadded dropwise 1M solution of methyl magnesium bromide in THF 500 mLunder ice-cooling. The reaction mixture was stirred under ice-coolingfor 2 hours. The resulting reaction mixture was added 2N hydrochloricacid under ice-cooling, and the mixture was stirred for 30 minutes. Themixture was made pH 8 by adding 1N aqueous sodium hydroxide solution,and the mixture was then extracted with ethyl acetate. The resultingorganic layers were washed with saturated brine, and the organic layerswere dried over anhydrous sodium sulfate. The organic layers wereconcentrated under reduced pressure to give an intermediate compound 158 g.

Intermediate compound 1: ¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 7.80 (1H, dd),7.38 (1H, dd), 2.70 (3H, s).

Preparation Example 2

To a suspension of sodium hydride (in oil, 60%) 57 g and DMF 560 mL wasadded dropwise ethanethiol 100 mL under ice-cooling. To the resultingmixture was added dropwise a mixture of the intermediate compound 1 204g and DMF 190 mL under ice-cooling. The resulting reaction mixture wasstirred for 1 hour under ice-cooling, and the mixture was added to icewater. The precipitated out solids were filtered, and washed with water.The obtained solids were dissolved into ethyl acetate, and the resultingsolutions were washed with saturated brine, and the organic layers weredried over sodium sulfate. The resulting organic layers wereconcentrated under reduced pressure, and the obtained solids were thenwashed with hexane to give an intermediate compound 2 160 g.

Intermediate compound 2:

¹H-NMR (CDCl₃) δ: 8.40 (1H, dd), 7.69 (1H, dd), 7.37 (1H, dd), 2.92 (2H,q), 2.72 (3H, s), 1.40 (3H, t).

Preparation Example 3

To a mixture of the intermediate compound 2 5.4 g, glyoxylic acidmonohydrate 2.8 g, and methanol 90 mL was added dropwise a mixedsolution of sodium hydroxide 2.4 g and methanol 60 mL under ice-cooling.The reaction mixture was stirred at 60° C. for 2 hours. The reactionmixture was allowed to stand to cool to room temperature, and theretowere then added acetic acid 11 mL and hydrazine monohydrate 2.3 gsuccessively. The resulting mixture was stirred at 100° C. for 19 hours.The resulting mixture was allowed to stand to cool to room temperature,and thereto was then added saturated aqueous ammonium chloride solution,and the mixture was extracted with chloroform. The resulting organiclayers were dried over sodium sulfate, and concentrated under reducedpressure. The resulting residue was subjected to silica gelchromatography to give an intermediate compound 3 3.8 g.

Intermediate compound 3: ¹H-NMR (CDCl₃) δ: 10.60 (1H, br s), 8.43 (1H,dd), 8.13 (1H, d), 7.71 (1H, dd), 7.29 (1H, dd), 7.05 (1H, d), 2.95 (2H,q), 1.35 (3H, t).

Preparation Example 4

To a mixture of the intermediate compound 3 4.2 g and chloroform 60 mLwas added 70% mCPBA 8.7 g under ice-cooling. The mixture was warmed toroom temperature, and then stirred for 12 hours. To the resultingreaction mixture were added saturated aqueous sodium hydrogen carbonatesolution, and aqueous sodium thiosulfate solution, and the mixture wasextracted with chloroform. The resulting organic layers were dried overanhydrous sodium sulfate, and concentrated under reduced pressure togive an intermediate compound 4 represented by the following formula 4.7g.

Intermediate compound 4: ¹H-NMR (CDCl₃) δ: 11.66 (1H, s), 8.90 (1H, dd),8.49 (1H, dd), 7.78 (1H, d), 7.61 (1H, dd), 7.10 (1H, d), 3.66 (2H, q),1.38 (3H, t).

Preparation Example 5

To a mixture of the intermediate compound 4 2.0 g and toluene 8 mL wasadded one drop of DMF and phosphorus oxybromide 4.3 g successively. Themixture was stirred at 100° C. for 9 hours. The resulting mixture wasallowed to stand to cool to room temperature, and water was then addedthereto, and the mixture was extracted with chloroform. The resultingorganic layers were washed with water and saturated brine, dried oversodium sulfate, and concentrated under reduced pressure. The resultingresidue was subjected to silica gel chromatography to give anintermediate compound 5 represented by the following formula 2.1 g.

Intermediate compound 5: ¹H-NMR (CDCl₃) δ: 8.93 (1H, dd), 8.54 (1H, dd),7.88-7.81 (2H, m), 7.66 (1H, dd), 3.89 (2H, q), 1.40 (3H, t).

Preparation Example 6

A mixture of the intermediate compound 5 300 mg, 3,5-difluorophenylboronic acid 170 mg, tris(dibenzylideneacetone)palladium(0) 42 mg,4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene 53 mg, trisodiumphosphate 12 hydrates 1.0 g, and dimethoxyethane 2 mL was stirred underheating at 80° C. for 7.5 hours. The resulting reaction mixture wasallowed to stand to cool to room temperature, and thereto was then addedsaturated aqueous sodium hydrogen carbonate solution, and the mixturewas extracted with ethyl acetate. The resulting organic layers werewashed with water and saturated brine, dried over sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel chromatography to give a compound 2 represented by thefollowing formula 230 mg.

Compound 2: ¹H-NMR (CDCl₃) δ: 8.97-8.95 (1H, m), 8.58-8.55 (1H, m), 8.07(1H, d), 8.00 (1H, d), 7.74-7.64 (3H, m), 7.02-6.96 (1H, m), 3.97 (2H,q), 1.44 (3H, t).

Preparation Example 7

The compounds that were prepared according to the similar method to thePreparation Example 6, and their physical property values are shownbelow.

A compound represented by formula (X):

[wherein, each of A¹, R⁴⁰, R⁴¹, R⁴², R⁴³, and R⁴⁴ represents any groupindicated in Table 18].

TABLE 18 Compound A¹ R⁴⁰ R⁴¹ R⁴² R⁴³ R⁴⁴ 1 N H CF₃ H CF₃ H 3 N H Cl H ClH 4 N H CF₃ H H H 5 N H H CF₃ H H

Compound 1: ¹H-NMR (CDCl₃) δ: 8.98 (1H, dd), 8.64 (2H, s), 8.58 (1H,dd), 8.17-8.11 (2H, m), 8.06 (1H, s), 7.69 (1H, dd), 3.98 (2H, q), 1.45(3H, t).

Compound 3: ¹H-NMR (CDCl₃) δ: 8.96 (1H, d), 8.56 (1H, d), 8.09-7.98 (4H,m), 7.66 (1H, dd), 7.53 (1H, d), 3.97 (2H, q), 1.43 (3H, t).

Compound 4: ¹H-NMR (CDCl₃) δ: 8.97 (1H, dd), 8.57 (1H, dd), 8.44 (1H,s), 8.32 (1H, d), 8.11-8.05 (2H, m), 7.81 (1H, d), 7.74-7.64 (2H, m),3.98 (2H, q), 1.44 (3H, t).

Compound 5: ¹H-NMR (CDCl₃) δ: 8.96 (1H, d), 8.57 (1H, d), 8.26 (2H, d),8.08 (2H, s), 7.83 (2H, d), 7.67 (1H, dd), 3.98 (2H, q), 1.44 (3H, t).

Preparation Example 8

To a mixture of 1.6 m butyl lithium-hexane solution 54 mL and THF 41 mLwas added dropwise a mixture of ethyl methyl sulfone 9.3 g and THF 24 mlat −78° C. To the reaction mixture was added dropwise a mixture of5-bromo-2-cyanopyridine 12 g and THF 41 mL at −78° C. The mixture waswarmed gradually to room temperature, and to the reaction mixture wasadded 2N hydrochloric acid, and the mixture was stirred for 30 minutes.The resulting mixture was extracted with ethyl acetate, and theresulting organic layers were washed with saturated brine. The resultingorganic layers were dried over anhydrous sodium sulfate, andconcentrated under reduced pressure to give an intermediate compound 6represented by the following formula 13 g.

Intermediate compound 6: ¹H NMR (CDCl₃): δ 8.79 (1H, d), 8.04-7.98 (2H,m), 4.97 (2H, s), 3.28 (2H, q), 1.46 (3H, t).

Preparation Example 9

The compound that was prepared according to the similar method to thePreparation Example 8, and its physical property value is shown below.

A compound represented by formula (X-2):

[wherein, each of L¹, A², A³ and A⁴ represents any group indicated inTable 19.]

TABLE 19 Intermediate compound L¹ A² A³ A⁴ 7 Br CH CH N

Intermediate compound 7: ¹H NMR (CDCl₃): δ 9.04 (2H, s), 4.96 (2H, s),3.29 (2H, q), 1.47 (3H, t)

Preparation Example 10

To a mixture of oxalyl chloride 8.9 mL and chloroform 68 ml was addeddropwise DMF 8 ml under ice-cooling. The mixture was stirred for 30minutes under ice-cooling, and then stirred at room temperature for 1.5hours. The mixture was cooled in ice bath, and thereto was then addeddropwise butyl vinyl ether 26 mL. The mixture was warmed to roomtemperature and stirred for 2 hours, and to the mixture was addeddropwise a mixture of the intermediate compound 1 10 g, triethylamine 33mL, and chloroform 23 ml under ice-cooling. The mixture was warmed toroom temperature and then stirred for 1.5 hours. The resulting mixturewas added to saturated aqueous ammonium chloride solution, and themixture was extracted with chloroform. The resulting organic layers werewashed with water and saturated brine, dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residuewas diluted with ethanol 10 mL, and thereto was added 28% ammonia water10 mL at room temperature. The mixture was warmed to 60° C. and stirredunder heating for 3 hours, and the mixture was allowed to stand to coolto room temperature, and then added to saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate.The resulting organic layers were dried over anhydrous sodium sulfate,and concentrated under reduced pressure. The resulting residue wassubjected to silica gel chromatography to give an intermediate compound8 represented by the following formula 4.5 g.

Intermediate compound 8: ¹H NMR (CDCl₃): δ 8.87 (1H, dd), 8.68 (1H, d),8.49 (1H, dd), 8.01-7.98 (m, 1H), 7.74 (1H, d), 7.56 (1H, dd), 3.86 (2H,q), 1.37 (3H, t).

Preparation Example 11

The compounds that were prepared according to the similar method to thePreparation Example 10, and their physical property values are shownbelow.

A compound represented by formula (X-3):

[wherein, each of L¹, A¹, A², A³ and A⁴ represents any groups indicatedin Table 20].

TABLE 20 Intermediate compound L¹ A¹ A² A³ A⁴ 9 OCH₃ N CH N CH 10 Br NCH CH N

Intermediate compound 9: ¹H-NMR (CDCl₃) δ: 8.74 (1H, dd), 8.66 (1H, dd),8.49 (1H, d), 8.20 (1H, d), 7.55 (1H, dd), 4.05 (3H, s), 3.85 (2H, q),1.38 (3H, t).

Intermediate compound 10: ¹H-NMR (CDCl₃) δ: 8.98 (1H, dd), 8.95 (2H, s),8.46 (1H, dd), 7.65 (1H, dd), 3.75 (2H, q), 1.38 (3H, t).

Preparation Example 12

A mixture of the intermediate compound 8 1.3 g,3,5-bis(trifluoromethyl)phenyl boronic acid 1.3 g,tetrakis(triphenylphosphine)palladium(0) 0.46 g, 2M aqueous sodiumcarbonate solution 11 mL, and toluene 40 mL was stirred under heating at130° C. for 14 hours. The resulting reaction mixture was allowed tostand to cool to room temperature, and thereto was then added saturatedaqueous sodium hydrogen carbonate solution, and the mixture wasextracted with ethyl acetate. The resulting organic layers were washedwith water and saturated brine, dried over sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel chromatography to a compound 21 represented by thefollowing formula 540 mg.

Compound 21: ¹H NMR (CDCl₃): δ 8.92 (1H, dd), 8.59 (1H, d), 8.53 (1H,dd), 8.07 (1H, brs), 7.96-7.91 (2H, m), 7.85 (1H, dd), 7.62-7.58 (2H,m), 3.90 (2H, q), 1.38 (3H, t).

Preparation Example 13

The compounds that were prepared according to the similar method to thePreparation Example 12, and their physical property values are shownbelow.

A compound represented by formula (X-4):

[wherein, each of A¹, R⁴⁰, R⁴¹, R⁴², R⁴³, and R⁴⁴ represents any groupindicated in Table 21.]

TABLE 21 Compound A¹ R⁴⁰ R⁴¹ R⁴² R⁴³ R⁴⁴ 6 N H H CF₃ H H 7 N H CF₃ H H H8 N H CF₃ Cl H H 9 N CF₃ H Cl H H 10 N H Cl H Cl H 11 N H F H F H 12 N HF F F H 13 N H OCF₃ H H H 14 N H Cl H H H 15 N F H CF₃ H H 20 N CF₃ HCF₃ H H

Compound 6: ¹H NMR (CDCl₃): δ 8.92-8.86 (2H, m), 8.52 (1H, dd), 8.08(1H, dd), 7.97-7.95 (1H, m), 7.77 (4H, brs), 7.58 (1H, dd), 3.95 (2H,q), 1.40 (3H, t).

Compound 7: ¹H NMR (CDCl₃): δ 8.92-8.86 (2H, m), 8.52 (1H, dd), 8.09(1H, dd), 8.09 (1H, dd), 7.97 (1H, dd), 7.90-7.83 (1H, m), 7.71-7.64(1H, m), 7.62-7.26 (2H, m), 3.96 (2H, q), 1.40 (3H, t).

Compound 8: ¹H NMR (CDCl₃): δ 8.92-8.89 (1H, dd), 8.84 (1H, d), 8.52(1H, dd), 8.05 (1H, dd), 7.96 (2H, dd), 7.75 (1H, dd), 7.65 (1H, d),7.58 (1H, dd), 3.94 (2H, q), 1.40 (3H, t).

Compound 9: ¹H NMR (CDCl₃): δ 8.92 (1H, dd), 8.57-8.51 (2H, m),7.93-7.91 (1H, m), 7.84-7.8 (2H, m), 7.64-7.57 (2H, m), 7.39 (1H, d),3.96 (2H, q), 1.38 (3H, t).

Compound 10: ¹H NMR (CDCl₃): δ 8.90 (1H, dd), 8.84 (1H, d), 8.52 (1H,dd), 8.02 (1H, dd), 7.95 (1H, d), 7.57 (1H, dd), 7.53 (2H, d), 7.44-7.43(1H, m), 3.93 (2H, q), 1.40 (3H, t).

Compound 11: ¹H NMR (CDCl₃): δ 8.90 (1H, dd), 8.82 (1H, d), 8.52 (1H,dd), 8.03 (1H, dd), 7.95 (1H, dd), 7.55 (1H, dd), 7.18 (2H, dd),6.91-6.86 (1H, m), 3.94 (2H, q), 1.40 (3H, t).

Compound 12: ¹H NMR (CDCl₃): δ 8.90 (1H, dd), 8.78-8.77 (1H, m), 8.51(1H, dd), 7.99-7.93 (2H, m), 7.58 (1H, dd), 7.31-7.23 (2H, m), 3.95 (2H,q), 1.39 (3H, t).

Compound 13: ¹H NMR (CDCl₃): δ 8.91 (1H, dd), 8.84 (1H, dd), 8.52 (1H,dd), 8.06 (1H, dd), 7.95 (1H, dd), 7.6-7.5 (4H, m), 7.31-7.26 (1H, m),3.96 (2H, q), 1.40 (3H, t).

Compound 14: ¹H NMR (CDCl₃): δ 8.9 (1H, dd), 8.83 (1H, dd), 8.51 (1H,dd), 8.04 (1H, dd), 7.94 (1H, dd), 7.65-7.64 (1H, m), 7.59-7.52 (2H, m),7.46-7.39 (2H, m), 3.95 (2H, q), 1.40 (3H, t).

Compound 15: ¹H NMR (CDCl₃): δ 8.91 (1H, dd), 8.82 (1H, brs), 8.52 (1H,dd), 8.1-8.06 (1H, m), 7.97 (1H, d), 7.67 (1H, t), 7.61-7.48 (3H, m),3.94 (2H, q), 1.4 (3H, t).

Compound 20: ¹H NMR (CDCl₃): δ 8.92 (1H, dd), 8.59 (1H, d), 8.53 (1H,dd), 8.07 (1H, brs), 7.96-7.91 (2H, m), 7.85 (1H, dd), 7.62-7.58 (2H,m), 3.90 (2H, q), 1.38 (3H, t).

Preparation Example 14

A mixture of the intermediate compound 8 1.0 g,5-chloro-2-(trimethylstannyl)pyridine 1.3 g, copper iodide 0.13 g,lithium chloride 0.19 g, tetrakis(triphenylphosphine)palladium(0) 0.14g, and toluene 50 mL was stirred under heating at 110° C. for 12 hours.The resulting reaction mixture was allowed to stand to cool to roomtemperature, and thereto was then added saturated aqueous sodiumhydrogen carbonate solution, and the mixture was extracted with ethylacetate. The resulting organic layers were washed with water andsaturated brine, dried over sodium sulfate, and concentrated underreduced pressure. The resulting residue was subjected to silica gelchromatography to give a compound 16 represented by the followingformula 500 mg.

Compound 16: ¹H NMR (CDCl₃): δ 9.24 (1H, d), 8.9 (1H, dd), 8.7 (1H, d),8.51 (1H, dd), 8.45 (1H, dd), 7.96 (1H, d), 7.79 (2H, d), 7.57 (1H, dd),3.94 (2H, q), 1.39 (3H, t).

Preparation Example 15

The compounds that were prepared according to the similar method to thePreparation Example 14, and their physical property values are shownbelow.

A compound represented by formula (X-5):

[wherein, each of A¹, A⁵, A⁶, A⁷, R⁴³, and R⁴⁴ represents any groupindicated in Table 22].

TABLE 22 Compound A¹ A⁵ A⁶ A⁷ R⁴³ R⁴⁴ 17 N CH N CCl H H 18 N CH CCl N HH 19 N CH CCl N Cl H

Compound 17: ¹H NMR (DMSO-d6): δ 9.07 (1H, d), 8.99 (1H, dd), 8.92 (1H,d), 8.47 (1H, dd), 8.4-8.35 (2H, m), 7.93 (1H, d), 7.82-7.79 (1H, m),7.70 (1H, d), 3.95 (2H, q), 1.26 (3H, t).

Compound 18: ¹H NMR (CDCl₃): δ 8.91 (2H, dd), 8.88 (1H, dd), 8.50 (1H,dd), 8.10 (1H, dd), 7.99 (1H, dd), 7.63-7.59 (2H, m), 7.51 (1H, dd),3.92 (2H, q), 1.40 (3H, t).

Compound 19: ¹H NMR (CDCl₃): δ 8.92-8.86 (2H, m), 8.52 (1H, d), 8.08(1H, dd), 8.01 (1H, d), 7.62-7.55 (1H, m), 7.59 (2H, s), 3.92 (2H, q),1.40 (3H, t).

Preparation Example 16

A mixture of methyl 5-chloro-2-pyradine carboxylate 10 g, sodiummethoxide (28% methanol solution) 28 mL, and THF 100 mL was stirred for3 hours under ice-cooling. To the resulting reaction mixture was addedethyl methyl sulfone 18 mL under ice-cooling. The reaction mixture waswarmed to 80° C., and stirred under heating for 24 hours. The resultingreaction mixture was allowed to stand to cool to room temperature, andthereto was then added 2N hydrochloric acid, and the mixture wasextracted with ethyl acetate. The resulting organic layers were driedover anhydrous sodium sulfate, and concentrated. The resulting residuewas subjected to silica gel chromatography to give an intermediatecompound 11 represented by the following formula 11 g.

Intermediate compound 11: ¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.25 (1H, d),4.87 (2H, s), 4.08 (3H, s), 3.29 (2H, q), 1.47 (3H, t).

Preparation Example 17

A mixture of the intermediate compound 9 4.5 g, and 12 N hydrochloricacid 20 mL was stirred under heating at 100° C. for 1 hour. The reactionmixture was allowed to stand to cool to room temperature, and theretowas then added ice water 100 mL. The mixture was alkalified by addingsaturated aqueous sodium hydrogen carbonate solution, and the mixturewas extracted with ethyl acetate. The resulting organic layers weredried over anhydrous sodium sulfate, and concentrated under reducedpressure. The resulting residue was subjected to silica gelchromatography to give an intermediate compound 12 represented by thefollowing formula 4.3 g.

Intermediate compound 12: ¹H-NMR (CDCl₃) δ: 8.81 (1H, dd), 8.47 (1H,dd), 8.21 (1H, d), 7.97 (1H, d), 7.52 (1H, dd), 3.83 (2H, q), 1.39 (3H,t).

Preparation Example 18

A mixture of the intermediate compound 12 4.3 g, phosphorus oxychloride12 mL, and toluene 60 ml was stirred under heating at 100° C. for 2hours. The resulting reaction mixture was allowed to stand to cool toroom temperature, and then concentrated under reduced pressure. To theresulting residue was added water, and the mixture was extracted withchloroform. The resulting organic layers were dried over anhydroussodium sulfate, and concentrated under reduced pressure to give anintermediate compound 13 represented by the following formula 4.6 g.

Intermediate compound 13: ¹H-NMR (CDCl₃) δ: 8.94 (1H, dd), 8.90 (1H,dd), 8.59 (1H, d), 8.52 (1H, d), 7.65 (1H, dd), 3.81 (2H, q), 1.39 (3H,t).

Preparation Example 19

To a mixture of the intermediate compound 2.0 g, and toluene 8 mL wereadded one drop of DMF and phosphorus oxybromide 4.3 g successively atroom temperature. The mixture was stirred at 100° C. for 9 hours. Theresulting mixture was allowed to stand to cool to room temperature, andthere was then added water, and the mixture was extracted with ethylacetate. The resulting organic layers were washed with water andsaturated brine successively, dried over sodium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel chromatography to give an intermediate compound 14represented by the following formula 2.1 g.

Intermediate compound 14: ¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.87 (1H, s),8.67 (1H, s), 8.50 (1H, d), 7.62 (1H, q), 3.78 (2H, q), 1.37 (3H, t).

Preparation Example 20

A mixture of the intermediate compound 14 1.0 g,3,5-bis(trifluoromethyl)phenyl boronic acid 1.04 g,dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane adduct 0.22 g, sodium carbonate 0.96 g, DME 15 mL, andwater 3 mL was stirred at 80° C. under argon atmosphere for 16 hours.The resulting mixture was allowed to cool to room temperature, andthereto was then added saturated aqueous sodium hydrogen carbonatesolution, and the mixture was extracted with ethyl acetate. Theresulting organic layers were washed with water and saturated brinesuccessively, dried over sodium sulfate, and concentrated under reducedpressure. The resulting residue was subjected to silica gelchromatography to give a compound 22 represented by the followingformula 460 mg.

Compound 22: ¹H NMR (CDCl₃) δ 1.42 (3H, t), 3.89 (2H, q), 7.65 (1H, dd),8.00 (1H, s), 8.54 (1H, d), 8.59 (2H, s), 8.97 (1H, d), 9.11 (1H, s),9.22 (1H, s).

Preparation Example 21

The compounds that were prepared according to the similar method to thePreparation Example 20, and their physical property values are shownbelow.

A compound represented by formula (X-5):

[wherein, each of A⁶, A⁷, R⁴⁰, R⁴³, and R⁴⁴ represents any groupindicated in Table 23].

TABLE 23 Compound A⁶ A⁷ R⁴⁰ R⁴³ R⁴⁴ 23 CH CH H CF₃ H 24 CH CCF₃ H H H 25N CH H CF₃ H 26 N CCF₃ H H H 27 CH N H CF₃ H 28 CH CH H OCF₃ H 29 CHC(OCF₃) H H H

Compound 23: ¹H NMR (CDCl₃) δ 1.41 (3H, t), 3.91 (2H, q), 7.61-7.70 (2H,m), 7.76 (1H, d), 8.30 (1H, d), 8.38 (1H, s), 8.50-8.57 (1H, m),8.92-8.99 (1H, m), 9.03-9.09 (1H, m), 9.16-9.22 (1H, m).

Compound 24: ¹H NMR (CDCl₃) δ 1.41 (3H, t), 3.90 (2H, q), 7.63 (1H, dd),7.79 (2H, d), 8.22 (2H, d), 8.54 (1H, d), 8.96 (1H, d), 9.05 (1H, s),9.19 (1H, s).

Compound 25: ¹H NMR (CDCl₃) δ 1.42 (3H, t), 3.89 (2H, q), 7.65 (1H, dd),8.54 (1H, dd), 8.70 (1H, s), 8.95-8.98 (1H, m), 9.01 (1H, s), 9.11 (1H,d), 9.22 (1H, d), 9.51 (1H, s).

Compound 26: ¹H NMR (CDCl₃) δ 1.42 (3H, t), 3.89 (2H, q), 7.65 (1H, dd),7.87 (1H, d), 8.54 (1H, dd), 8.62 (1H, d), 8.97 (1H, dd), 9.09 (1H, d),9.23 (1H, d), 9.41 (1H, s)

Compound 27: ¹H NMR (CDCl₃) δ 1.42 (3H, t), 3.88 (2H, q), 7.64-7.67 (1H,m), 8.20 (1H, d), 8.41 (1H, s), 8.53 (1H, d), 8.92 (1H, d), 8.97 (1H,d), 9.13 (1H, s), 9.23 (1H, s).

Compound 28: ¹H NMR (CDCl₃) δ 1.42 (3H, t), 3.90 (2H, q), 7.35 (1H, d),7.57 (1H, t), 7.62-7.64 (1H, m), 7.99 (1H, s), 8.03 (1H, d), 8.52 (1H,d), 8.95 (1H, d), 9.01 (1H, s), 9.17 (1H, s).

Compound 29: ¹H NMR (CDCl₃) δ 1.40 (3H, t), 3.90 (2H, q), 7.37 (2H, d),7.58-7.63 (1H, m), 8.14 (2H, d), 8.53 (1H, d), 8.95 (1H, d), 9.00 (1H,s), 9.16 (1H, s).

Preparation Example 22

A mixture of the intermediate compound 14 0.8 g, lithiumtrihydroxy[4-(trifluoromethyl)pyridin-2-yl]borate 1.04 g, copper(I)chloride 24 mg, zinc chloride 322 mg,dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II)dichloromethane adduct 178 mg, cesium carbonate 1.58 g, and DMF 15 mLwas stirred at 100° C. under argon atmosphere for 16 hours. Theresulting mixture was allowed to stand to cool to room temperature, andthe mixture was then extracted with ethyl acetate. The resulting organiclayers were washed with water and saturated brine successively, driedover sodium sulfate, and concentrated under reduced pressure. Theresulting residue was subjected to silica gel chromatography to give acompound 30 represented by the following formula 250 mg.

Compound 30: ¹H NMR (CDCl₃) δ 1.40 (3H, t), 3.89 (2H, q), 7.61-7.64 (2H,m), 8.53 (1H, d), 8.72 (1H, s), 8.87-8.96 (2H, m), 9.15 (1H, s), 9.67(1H, s).

Preparation Example 15

The compound that was prepared according to the similar method to thePreparation Example 22, and its physical property value is shown below.

A compound represented by formula (X-6):

[wherein, each of A⁵, A⁶, A⁷, R⁴³, and R⁴⁴ represents any groupindicated in Table 24.]

TABLE 24 Compound A⁵ A⁶ A⁷ R⁴³ R⁴⁴ 31 N CCF₃ CH H H

Compound 31: ¹H NMR (CDCl₃) δ 1.28 (3H, t), 3.92 (2H, q), 7.61-7.64 (1H,m), 7.76 (1H, d), 8.05 (1H, t), 8.53 (1H, d), 8.66 (1H, d), 8.94 (1H,d), 9.14 (1H, s), 9.71 (1H, s).

Next, the formulation examples of the compound of the present inventionare shown below. The “parts” represents “part by weight” unlessotherwise specified.

Formulation Example 1

Into a mixture of 35 parts of xylene and 35 parts of DMF, 10 parts ofany one of the compounds 1 to 31 is dissolved, and then 14 parts ofpolyoxyethylene styryl phenyl ether and 6 parts of calciumdodecylbenzene sulfonate are added, followed by mixing them to obtaineach formulation.

Formulation Example 2

Four (4) parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrated silicon oxide fine powder and54 parts of diatomaceous earth are mixed, and further 20 parts of anyone of the compounds 1 to 31 is added, followed by mixing them to obtaineach wettable powders.

Formulation Example 3

To 2 parts of any one of the compounds 1 to 31, 1 part of synthetichydrated silicon oxide fine powder, 2 parts of calcium lignin sulfonate,30 parts of bentonite and 65 parts of kaolin clay are added, followed bymixing, granulation with a granulator and forced-air drying to obtaineach granular formulation.

Formulation Example 4

Into an appropriate amount of acetone, 1 part of any one of thecompounds 1 to 31 is mixed, and then 5 parts of synthetic hydroussilicon oxide fine powder, 0.3 parts of isopropyl acid phosphate and93.7 parts of kaolin clay are added, followed by mixing with stirringthoroughly and removal of acetone from the mixture by evaporation toobtain each of powder formulation.

Formulation Example 5

A mixture of 35 parts of polyoxyethylene alkyl ether sulfate ammoniumsalt and white carbon (weight ratio of 1:1), 20 parts of any one of thecompounds 1 to 31, and 45 parts of water are mixed, followed by finelygrounding by a wet grinding method to obtain each flowable formulation.

Formulation Example 6

Into a mixture of 5 parts of xylene and 5 parts of trichloroethane, 0.1parts of any one of the compounds 1 to 31 is dissolved, and theresulting mixture is then mixed with 89.9 parts of kerosene to obtaineach oil solution.

Formulation Example 7

Into 0.5 mL of acetone, 10 mg of any one of the compounds 1 to 31 isdissolved and the solution is added dropwise to 5 g of a solid feedpowder for an animal (solid feed powder for rearing and breeding CE-2,manufactured by CLEA Japan, Inc.), followed by mixing the resultingmixture uniformly, and then by drying them by evaporation of acetone toobtain each poison bait.

Formulation Example 8

Into an aerosol can, 0.1 part of any one of the compounds 1 to 31 and49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) are placed. Aftermounting an aerosol valve, 25 parts of dimethylether and 25 parts of LPGare filled, followed by shaking and further mounting an actuator toobtain an oily aerosol.

Formulation Example 9

A mixture of 0.6 part of any one of the compounds 1 to 31, 0.01 part ofBHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 parts ofdeodorized kerosine and 1 part of an emulsifier {Rheodol MO-60(registered trademark of Kao Corporation)} and 50 parts of distilledwater are filled into an aerosol container, and a valve part isattached. Then, 40 parts of a propellant (LPG) is filled therein throughthe valve under pressure to obtain an aqueous aerosol.

Formulation Example 10

Zero point one (0.1) parts of any one of the compounds 1 to 31 are mixedinto 2 mL of propylene glycol, and the resulting solution is impregnatedinto a ceramic plate having a size of 4.0 cm×4.0 cm and a thickness of1.2 cm, to obtain thermal fumigants.

Formulation Example 11

Five (5) parts of any one of the compounds 1 to 31, and 95 parts ofethylene-methyl methacrylate copolymer (the ratio of the methylmethacrylate in the copolymer: 10 weight %), Acryft (registered bytrademark) WD 301, manufactured by Sumitomo Chemical Co. Ltd.) aremelted and kneaded with a closed type pressure kneader (manufactured byMoriyama Manufacturing Co. Ltd.), and the resulting kneaded product isextruded from an extrusion molding machine through a molding die toobtain a rod-shaped molded product having a length of 15 cm and adiameter of 3 mm.

Formulation Example 12

Five (5) parts of any one of the compounds 1 to 31, and 95 parts ofplasticized polyvinyl chloride resin are melted and kneaded with aclosed type pressure kneader (manufactured by Moriyama Manufacturing Co.Ltd.), and the resulting kneaded product is extruded from an extrusionmolding machine through a molding die to obtain a rod-shaped moldedproduct having a length of 15 cm and a diameter of 3 mm.

Formulation Example 13

One hundred (100) mg of any one of the compounds 1 to 31, 68.75 mg oflactose, 237.5 mg of corn starch, 43.75 mg of microcrystallinecellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodiumcarbomethyl starch and 2.5 mg of magnesium stearate are mixed, and theresulting mixture was compressed to an appropriate size to obtain atablet.

Formulation Example 14

Twenty five (25) mg of any one of the compounds 1 to 31, 60 mg oflactose, 25 mg of corn starch, 6 mg of carmellose calcium and anappropriate amount of 5% of hydroxypropyl methylcellulose are mixed, andthe resulting mixture are filled into a hard shell gelatin capsule or ahydroxypropyl methylcellulose capsule to obtain capsules.

Formulation Example 15

To 100 mg of any one of the compounds 1 to 31, 500 mg of fumaric acid,2000 mg of sodium chloride, 150 mg of methyl paraben, 50 mg of propylparaben, 25000 mg of granulated sugar, 13,000 mg of sorbitol (70%solution), 100 mg of Veegum K (manufactured by Vanderbilt Co.), 35 mg ofperfume and 500 mg of coloring agent, a distilled water is added so thata final volume is set to be 100 mL, followed by mixing them to obtain asuspension for oral administration.

Formulation Example 16

Into a mixture of 5% by weight of an emulsifier, 3% by weight of benzylalcohol and 30% by weight of propylene glycol, 5% by weight of any oneof the compounds 1 to 31 is dissolved, and phosphate buffer is addedthereto so that a pH of the solution is set to be 6.0 to 6.5, and wateris added as the rest parts to obtain the solution for oraladministration.

Formulation Example 17

To a mixture of 57% by weight of fractional distillated palm oil and 3%by weight of polysorbate 85, 5% by weight of aluminum distearate isadded, and heated to disperse it. The resulting mixture is cooled toroom temperature, and 25% by weight of saccharin is dispersed in an oilvehicle. Ten (10) % by weight of any one of the compounds 1 to 31 isdivided thereto to obtain a paste for oral administration.

Formulation Example 18

Five (5) % by weight of any one of the compounds 1 to 31 is mixed with95% by weight of limestone filler, followed by a wet granulation of theresulting mixture to obtain a granule for oral administration.

Formulation Example 19

Into 80 parts of diethylene glycol monomethyl ether, 5 parts of any oneof the compounds 1 to 31 is dissolved, and 15 parts of propylenecarbonate is added thereto, and the resulting mixture is mixed to obtaina spot-on solution.

Formulation Example 20

Into 70 parts of diethylene glycol monomethyl ether, 10 parts of any oneof the compounds 1 to 31 is dissolved, and 20 parts of 2-octyldodecanolis added thereto, and the resulting mixture is mixed to obtain a pour-onsolution.

Formulation Example 21

To 0.5 parts of any one of the compounds 1 to 31, 60 parts of Nikkol(registered by trademark) TEALS-42 (manufactured by Nikko Chemical Co.Ltd.: 42% of aqueous solution of lauryl sulfuric acid triethanol amine)and 20 parts of propylene glycol are added, and the resulting mixture ismixed with stirring thoroughly, and 19.5 parts of water is then addedthereto and the resulting mixture is further mixed with stirringthoroughly to obtain a hydrogenous solution of shampoo formulation.

Formulation Example 22

Zero point fifteen (0.15) % by weight of any one of the compounds 1 to31, 95% by weight of animal feed, as well as 4.85% by weight of amixture of dibasic calcium phosphate, diatomaceous earth, aerosol andcarbonate (or chalk) are mixed with stirring thoroughly to obtain apremix for animal feed.

Formulation Example 23

Seven point two (7.2) g of any one of the compounds 1 to 31, and 92.8 gof Hosco (registered trademark) S-55 (manufactured by MaruishiPharmaceuticals) are melted and mixed at 100° C., and the resultingmixture was poured into a suppository mold, followed by performing acooling solidification to obtain a suppository.

Next, Test Examples are used to show an efficacy of the Present compoundon controlling harmful arthropods.

The following test examples were carried out at 25° C.

Test Example 1

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water containing 0.03 v/v % of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.

Cucumber (Cucumis sativus) seedling (on the developmental stage of thesecond true leaf) is planted in a container and approximately 30 cottonaphids (Aphis gossypii) (all stages of life) are released onto theleaves of the cucumber. After 1 day, the diluted solutions are sprayedinto the seedling in a ratio of 10 mL/seedling. After 5 days, the numberof the surviving insects is examined and the controlling value iscalculated by the following equation.Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100wherein the symbols in the formula represent the following descriptions.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

Here the “untreated group” represents a group where the similartreatment procedure to that of the treated group except not using thetest compound is done.

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 1. As a result of the test, the below-mentionedcompounds showed 90% or greater as the controlling value.

Compound number: 1, 2, 4, 5, 7, 9, 10, 11, 12, 13, 16, 17, 19, 21, 22,23, 24, 25, 26, 27, 28, 29 and 31

Test Example 2

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water containing 0.03 v/v % of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.

Rice (Oryza sativa) seedling (on the developmental stage of the secondtrue leaf) is planted in a container, and the diluted solutions aresprayed into the seedling in a ratio of 10 mL/seedling. Thereafter, 203rd instar larvae of brown planthopper (Nilaparvata lugens) are releasedonto the rice leaves. After 6 days, the number of the surviving insectsis examined, and the morality of insects is calculated by the followingequation.Morality (%)={1−the number of the surviving insects/20}×100

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 2. As a result of the test, the below-mentionedcompounds showed 90% or greater as the morality.

Compound number: 7, 11, 18, 23, 25, and 26

Test Example 3

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

In a container, 7.7 g of artificial diet (Insecta LF, manufactured byNOSAN CORPORATION) is placed, and 2 mL of the diluted solution isirrigated thereto. Five (5) fourth instar larvae of tobacco cutworm(Spodoptera litura) are released onto the artificial diet. After 5 days,the number of the surviving insects is examined, and the morality ofinsects is calculated by the following equation.Morality (%)={1−the number of the surviving insects/5}×100

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 3. As a result of the test, the below-mentionedcompounds showed 80% or greater as the morality.

Compound number: 1, 10 and 22

Test Example 4

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

The diluted solutions are sprayed into the cabbage (Brassicae oleracea)seedling (on the developmental stage of the second to third true leaf)that is planted in a container in a ratio of 20 mL/seedling. Thereafter,the stem and leaf thereof is cut out and then is installed into thecontainer that is covered with the filter paper. Five (5) cabbage moth(Plutella xylostella) at the second instar larval stages are releasedinto the cup. After 5 days, the number of the surviving insects iscounted, and the mortality of insects is calculated by the followingequation.Morality (%)={1−the number of the surviving insects/5}×100

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 4. As a result of the test, the below-mentionedcompounds showed 80% or greater as the morality.

Compound number: 1, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 22, 23, 24, 25, 26, 27, 30, and 31

Test Example 5

The test compounds are dissolved into a mixed solution ofpolyoxyethylene sorbitan mono-cocoate and acetone (acetone andpolyoxyethylene sorbitan mono-cocoate=5:95 (v/v ratio)) in a ratio of 50μL of the mixed solution per 1 mg of the test compound. Thereto is addedwater containing 0.03% by volume of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.

Corns (Zea mays) are sown on a tray overlaid with damped KimWipes(registered trademark). After corns were grown for 5 days, the entireseedling of the corn is immersed into the diluted solution for 30seconds. Thereafter, each two grains of the seedling are installed in aplastic petri dish (90 mm radius), and 10 western corn rootworms(Diabrotica virgifera virgifera) at the second instar larval stages arereleased onto the cup. After 5 days, the number of the died insects iscounted, and the mortality of insects is calculated by the followingequation.Morality (%)={1−the number of the surviving insects/10}×100

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 5. As a result of the test, the below-mentionedcompounds showed 80% or greater as the morality.

Compound number: 1, 6, 7, 8, 10, 12, 13, 21, 22, 23, 24, 25, 26, and 31

Test Example 6

The test compounds are dissolved into a mixed solution of xylene, DMFand surfactants (xylene, DMF and surfactants=4:4:1 (v/v ratio)) in aratio of 10 μL of the mixed solution per 1 mg of the test compound.Thereto is added water containing 0.03% by volume of a spreader toprepare a diluted solution containing a prescribed concentration of thetest compound.

The diluted solutions are sprayed into the cucumber seedling (CucumisSativus) (on the developmental stage of the second to third true leaf)that is planted in the container in a ratio of 10 mL/seedling.Thereafter, the second leaf is cut out, and then installed into thepolyethylene cup, and 10 cucurbit leaf beetles (Aulacophora femoralis)at the second instar larval stages are released into the container.After 5 days, the number of died insects is counted, and the mortalityof insects is calculated by the following equation.Mortality of insects (%)=(Number of dead insects/10)×100

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 6. As a result of the test, the below-mentionedcompounds showed 80% or greater as the morality.

Compound number: 4 and 5

Test Example 7

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

The container is matted with a filter paper having 5.5 cm diameter, and30 mg sucrose is placed on the filter paper, and 0.7 mL of the dilutedsolution is added dropwise to the filter paper. Ten (10) female adulthouseflies (Musca domestica) are released into the container. After 24hours, the number of died insects is counted, and the mortality ofinsects is calculated by the following equation.Mortality of insects (%)=(Number of dead insects/Number of testinsects)×100

The test was conducted by making the prescribed concentration 500 ppmand using the below-mentioned compounds as a test compound according tothe test example 7. As a result of the test, the below-mentionedcompounds showed 100% as the morality.

Compound number: 3, 4, and 5

INDUSTRIAL APPLICABILITY

The Present compound shows an excellent control effect against a harmfularthropod.

The invention claimed is:
 1. A compound represented by formula (I):

or an N-oxide compound thereof, wherein Het¹ represents Het¹-1:

R¹ represents OR⁴, OS(O)₂R⁴, S(O)_(m)R⁴, NR⁵S(O)₂R⁴, a C1-C4 chainhydrocarbon group having one or more halogen atoms, or a halogen atom;R⁴ represents a C1-C4 chain hydrocarbon group having one or more halogenatoms; R⁵ represents a hydrogen atom, or a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms; X¹ represents CR³⁰; X³represents CR³²; X⁴ represents CR³³; X⁵ represents CR³⁴; R³⁰, R³², R³³,and R³⁴ represent independently of each other a hydrogen atom, a C1-C6chain hydrocarbon group optionally having one or more halogen atoms, aC3-C6 alicyclic group optionally having one or more halogen atoms, or ahalogen atom, A¹ represents a nitrogen atom; A² represents a nitrogenatom, A³ represents CR⁷, and A⁴ represents CR⁸; R⁷ and R⁸ representindependently of each other a hydrogen atom, a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a nitro group, OR¹⁸,NR¹⁸R¹⁹, a cyano group, or a halogen atom; n is 0, 1, or 2; R²represents a cyclopropyl group, a cyclopropylmethyl group, or a C1-C6alkyl group optionally having one or more halogen atoms; q is 0, 1, 2,or 3; R³ represents a C1-C6 chain hydrocarbon group optionally havingone or more substituents selected from Group B, a phenyl groupoptionally having one or more substituents selected from Group D, anitro group, OR¹², NR¹¹R¹², NR²⁴NR¹¹R¹², NR²⁴OR¹¹, NR¹¹C(O)R¹³,NR²⁴NR¹¹C(O)R¹³, NR¹¹C(O)OR¹⁴, NR²⁴NR¹¹C(O)OR¹⁴, NR¹¹C(O)NR¹⁵R¹⁶,NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, N═CHNR¹⁵R¹⁶, N═S(O)_(x)R¹⁵R¹⁶, S(O)_(y)R¹⁵,C(O)OR¹⁷, C(O)NR¹¹R¹², a cyano group, or a halogen atom, and when q is 2or 3, two or more R³ is identical to or different from each other; R¹¹,R¹⁷, R¹⁸, R¹⁹ and R²⁴ represent independently of each other a hydrogenatom, or a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms; R¹² represents a hydrogen atom, S(O)₂R²³, a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, or aC1-C6 alkyl group having one substituent selected from Group F; R²³represents a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, or a phenyl group optionally having one or moresubstituents selected from Group D; R¹³ represents a hydrogen atom, aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a C3-C7 cycloalkyl group optionally having one or more halogenatoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one ormore halogen atoms, or a phenyl group optionally having one or moresubstituents selected from Group D; R¹⁴ represents a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, a C3-C7cycloalkyl group optionally having one or more halogen atoms, a (C3-C6cycloalkyl)C1-C3 alkyl group optionally having one or more halogenatoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety of thephenyl C1-C3 alkyl group may optionally have one or more substituentsselected from Group D; m is 0, 1, or 2; x is 0 or 1; y is 0, 1, or 2;Group B is selected from the group consisting of a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, a C1-C6 alkylsulfanyl groupoptionally having one or more halogen atoms, a C1-C6 alkylsulfinyl groupoptionally having one or more halogen atoms, a C1-C6 alkylsulfonyl groupoptionally having one or more halogen atoms, a C3-C6 cycloalkyl groupoptionally having one or more halogen atoms, a cyano group, a hydroxygroup, and a halogen atom; Group D is selected from the group consistingof a C1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a hydroxy group, a C1-C6 alkoxy group optionally having one ormore halogen atoms, a C3-C6 alkenyloxy group optionally having one ormore halogen atoms, a C3-C6 alkynyloxy group optionally having one ormore halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl groupoptionally having one or more halogen atoms, a C1-C6 alkylsulfinyl groupoptionally having one or more halogen atoms, a C1-C6 alkylsulfonyl groupoptionally having one or more halogen atoms, an amino group, NHR²¹,NR²¹R²², C(O)R²¹, OC(O)R²¹, C(O)OR²¹, a cyano group, a nitro group, anda halogen atom, wherein said R²¹ and R²² represent independently of eachother a C1-C6 alkyl group optionally having one or more halogen atoms.2. The compound according to claim 1, wherein R³ represents a C1-C6alkyl group optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group G,NR¹¹R¹², NR²⁴NR¹¹R¹² or a halogen atom, wherein Group G is selected fromthe group consisting of a halogen atom and a C1-C6 haloalkyl group. 3.The compound according to claim 1, wherein R³ represents a C1-C6 alkylgroup optionally having one or more halogen atoms, or a halogen atom. 4.The compound according to claim 1, wherein R² represents an ethyl group.5. The compound according to claim 1, wherein R¹ represents a C1-C4chain hydrocarbon group having one or more halogen atoms, or a halogenatom; R² represents a methyl group, or an ethyl group; and R³ representsa C1-C6 alkyl group optionally having one or more halogen atoms, aphenyl group optionally having one or more substituents selected fromGroup G, NR¹¹R¹², NR²⁴NR¹¹R¹², or a halogen atom; R¹¹, R¹² and R²⁴represent independently of each other a hydrogen atom, a C1-C3 alkylgroup optionally having one or more halogen atoms; R⁷ and R⁸ representindependently of each other a C1-C6 alkyl group optionally having one ormore halogen atoms, or a halogen atom; and q is 0 or 1; wherein Group Gis selected from the group consisting of a halogen atom and a C1-C6haloalkyl group.
 6. The compound according to claim 1, wherein R¹represents a C1-C4 chain hydrocarbon group having one or more halogenatoms, or a halogen atom; R² represents a methyl group, or an ethylgroup; R³ represents a C1-C6 alkyl group optionally having one or morehalogen atoms, a phenyl group optionally having one or more substituentsselected from Group G, NR¹¹R¹², NR²⁴NR¹¹R¹², or a halogen atom; R¹¹,R¹², and R²⁴ represent independently of each other a hydrogen atom, aC1-C3 alkyl group optionally having one or more halogen atoms; R⁷ and R⁸represent independently of each other a hydrogen atom, a C1-C6 alkylgroup optionally having one or more halogen atoms, or a halogen atom;and q is 0 or 1; wherein Group G is selected from the group consistingof a halogen atom and a C1-C6 haloalkyl group.
 7. The compound accordingto claim 1, wherein R¹ represents a C1-C4 chain hydrocarbon group havingone or more halogen atoms, or a halogen atom; R² represents an ethylgroup; q is 0 or 1; and R³ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom.
 8. A compositionfor controlling a harmful arthropod comprising the compound according toclaim 1 and an inert carrier.
 9. The compound according to claim 1,wherein R¹ is a C1-C4 chain hydrocarbon group having one or more halogenatoms, or a halogen atom; X¹ is CH, X³ is CR³², X⁴ is CR³³, and X⁵ isCH; R² is an ethyl group; and R³ is a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom.
 10. A compositionfor controlling a harmful arthropod comprising the compound according toclaim 9 and an inert carrier.